Microbiocidal oxadiazole derivatives

ABSTRACT

Compounds of the formula (I) wherein the substituents are as defined in claim  1 , useful as a pesticides, especially fungicides.

CROSS-REFERENCE TO RELATED APPLICATIONS

This application is a 371 National Stage application of InternationalApplication No. PCT/EP2016/073295, filed Sep. 29, 2016, which claimspriority to European Patent Application No. 15188238.8, filed Oct. 2,2015 and European Patent Application No. 16150491.5, filed Jan. 7, 2016,the entire contents of which are hereby incorporated by reference.

The present invention relates to microbiocidal oxadiazole derivatives,eg, as active ingredients, which have microbiocidal activity, inparticular, fungicidal activity. The invention also relates toagrochemical compositions which comprise at least one of the oxadiazolederivatives, to processes of preparation of these compounds and to usesof the oxadiazole derivatives or compositions in agriculture orhorticulture for controlling or preventing infestation of plants,harvested food crops, seeds or non-living materials by phytopathogenicmicroorganisms, preferably fungi.

Microbiocidal oxadiazole derivatives are known as insecticidal andacaricidal agents, eg, from CN 1927860. WO 2013/064079, EP 0 276 432 andWO 2015/185485 describe the use of substituted oxadiazoles for combatingphytopathogenic fungi.

According to the present invention, there is provided a compound offormula (I):

wherein

n is 1 or 2

A¹ represents N or CR¹, wherein R¹ is hydrogen, halogen, methyl, ethyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;

A² represents N or CR², wherein R² is hydrogen, halogen, methyl, ethyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;

A³ represents N or CR³, wherein R³ is hydrogen or halogen;

A⁴ represents N or CR⁴, wherein R⁴ is hydrogen or halogen; and

wherein 0, 1 or 2 of A¹, A², A³ and A⁴ are N;

R⁵ and R⁶ are independently selected from hydrogen, C₁₋₄alkyl, halogen,cyano, trifluoromethyl and difluoromethyl, or R⁵ and R⁶ together withthe carbon atom they share form a cyclopropyl;

R⁷ is hydroxy, C₁₋₄alkyl, C₁₋₄ haloalkyl, C₁₋₄alkoxy, hydroxyC₁₋₄alkyl,C₁₋₂alkoxyC₁₋₄alkyl, C₁₋₂haloalkoxyC₁₋₄alkyl, C₃₋₆alkenyl, C₃₋₄alkynyl,C₃₋₆alkenyloxy, C₃₋₆alkynyloxy, C₃₋₆ haloalkenyl, C₃₋₆haloalkenyloxy,C₁₋₄alkylcarbonyloxy, C₁₋₄ haloalkylcarbonyloxy, C₁₋₄alkoxycarbonyloxy,C₁₋₄alkylcarbonyloxyC₁₋₄alkyl, C₁₋₄ haloalkylcarbonyloxyC₁₋₄alkyl orC₁₋₄alkoxycarbonyloxyC₁₋₄alkyl; or

R⁷ is C₃₋₆cycloalkyl, C₃₋₆cycloalkylC₁₋₂alkyl, C₃₋₆cycloalkylC₁₋₂alkoxy,phenyl, phenylC₁₋₂alkyl, phenylC₁₋₂alkoxy, heteroaryl,heteroarylC₁₋₂alkyl, heteroarylC₁₋₂alkoxy, heterocyclyl,heterocyclylC₁₋₂alkyl, heterocyclylC₁₋₂alkoxy,C₃₋₆cycloalkylcarbonyloxy, heterocyclylcarbonyloxy phenylcarbonyloxy,C₃₋₆cycloalkylcarbonyloxyC₁₋₄alkyl, heterocyclylcarbonyloxyC₁₋₄alkyl orphenylcarbonyloxyC₁₋₄alkyl,

wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromaticring which comprises 1, 2, 3 or 4 heteroatoms individually selected fromN, O and S, the heterocyclyl moiety is a 4- to 6-membered non-aromaticring which comprises 1 or 2 heteroatoms individually selected from N, Oand S, and wherein any of said cycloalkyl, phenyl, heteroaryl andheterocyclyl moieties are optionally substituted by 1 or 2 substituentsselected from cyano, fluoro, chloro, bromo, methyl, difluoromethyl,trifluoromethyl, methoxy, ethoxy, or difluoromethoxy;

R⁸ is hydrogen, C₁₋₆alkyl, C₂₋₆alkenyl, C₂₋₆alkynyl, cyanoC₁₋₆alkyl,C₁₋₆ haloalkyl, C₂₋₆haloalkenyl, hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl,C₁₋₄ haloalkoxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl,C₂₋₄alkynyloxyC₁₋₆alkyl, aminoC₁₋₆alkyl, N—C₁₋₄alkylaminoC₁₋₆alkyl,N,N-diC₁₋₄alkylaminoC₁₋₆alkyl, C₁₋₆alkylcarbonylC₁₋₆alkyl,C₁₋₆alkylcarbonylC₂₋₆alkenyl, C₁₋₆alkoxycarbonylC₁₋₆alkyl,C₁₋₆alkylcarbonyloxyC₁₋₆alkyl, N—C₁₋₄alkylaminocarbonylC₁₋₆alkyl,N,N-diC₁₋₄alkylaminocarbonylC₁₋₆alkyl, C₁₋₆alkylsulfanylC₁₋₆alkyl,C₁₋₆alkylsulfonylC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₂₋₆alkynyl, C₂₋₆alkynyloxycarbonylaminoC₁₋₆alkyl,C₁₋₄alkylcarbonylaminoC₁₋₆alkyl or C₁₋₄alkoxycarbonylaminoC₁₋₆alkyl; or

R⁸ is C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₆alkyl, wherein the cycloalkylmoiety is optionally partially unsaturated, phenyl, phenylC₁₋₆alkyl,phenylC₂₋₆alkenyl, napthyl, naphthylC₁₋₆alkyl, heteroaryl,heteroarylC₁₋₆alkyl, wherein the heteroaryl moiety is a 5- or 6-memberedmonocyclic aromatic ring which comprises 1, 2, 3 or 4 heteroatomsindividually selected from N, O and S, heterodiaryl,heterodiarylC₁₋₆alkyl wherein the heterodiaryl moiety is a 9- or10-membered bicyclic aromatic system which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, heterocyclyl,heterocyclylC₁₋₆alkyl wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, orC₃₋₆cycloalkylcarbonylaminoC₁₋₆alkyl,

wherein for R⁸, any cycloalkyl, phenyl, napthyl, heteroaryl,heterodiaryl or heterocyclyl moiety is optionally substituted by 1, 2 or3 substituents, which may be the same or different, selected from R⁹;or, additionally, when R⁸ is cyclopropyl, the cyclopropyl moiety issubstituted by 4 substituents, which may be the same or different,selected from R⁹, with the proviso that at least 2 R⁹ substituents arethe same; wherein

R⁹ is cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl, C₁₋₄haloalkyl, C₂₋₄ haloalkenyl, C₁₋₄alkoxy, C₁₋₄ haloalkoxy,C₃₋₄alkynyloxy, N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino,C₁₋₄alkylcarbonyl, C₃₋₆cycloalkylcarbonyl, C₁₋₄alkoxycarbonyl,carbonylamino, N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl orC₁₋₄alkoxycarbonylamino, and wherein when R₈ is substitutedC₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₆alkyl, heterocyclyl, orheterocyclylC₁₋₆alkyl, R⁹ may also represent oxo on the C₃₋₈cycloalkylor heterocyclyl moiety; or

wherein for R⁸, any cycloalkyl, phenyl, napthyl, heteroaryl,heterodiaryl or heterocyclyl moiety is optionally substituted by 1substituent selected from R¹⁰ and further optionally substituted by 1 or2 substituents selected from R⁹; wherein

R¹⁰ is C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₂alkyl, phenyl, phenylC₁₋₂alkyl,heteroaryl, heteroarylC₁₋₂alkyl wherein the heteroaryl moiety is a 5- or6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, heterocyclyl orheterocyclylC₁₋₆alkyl wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein any of saidcycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R¹¹; wherein

R¹¹ is hydrogen, cyano, fluoro, chloro, bromo, methyl, trifluoromethyl,methoxy and ethoxy;

or

R⁸ represents —OR¹², wherein R¹² is hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl,C₃₋₆alkynyl, cyanoC₁₋₆alkyl, C₁₋₆ haloalkyl, C₃₋₆ haloalkenyl,hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₄ haloalkoxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl, aminoC₁₋₆alkyl,C₁₋₆alkylcarbonylC₁₋₆alkyl, C₁₋₆alkylcarbonylC₂₋₆alkenyl,C₁₋₆alkoxycarbonylC₁₋₆alkyl, C₁₋₆alkylcarbonyloxyC₁₋₆alkyl,N—C₁₋₄alkylaminocarbonylC₁₋₆alkyl,N,N-diC₁₋₄alkylaminocarbonylC₁₋₆alkyl, C₁₋₄alkylsulfanylC₁₋₆alkyl,C₁₋₆alkylsulfonylC₁₋₆alkyl or C₁₋₆alkylsulfonylaminoC₁₋₆alkyl; or

R¹² is C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₆alkyl, wherein the cycloalkylmoiety is optionally partially unsaturated, phenyl, phenylC₁₋₆alkyl,heteroaryl, heteroarylC₁₋₆alkyl, wherein the heteroaryl moiety is a 5-or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, heterocyclyl orheterocyclylC₁₋₆alkyl, wherein the heterocyclyl moiety is a 4-to6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S;

wherein for R¹², any cycloalkyl, phenyl, heteroaryl or heterocyclylmoiety is optionally substituted by 1, 2 or 3 substituents, which may bethe same or different, selected from R¹³; wherein

R¹³ is cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl,C₁₋₄ haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₄ haloalkoxy,C₃₋₄alkenyloxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino,C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, carbonylamino,N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl orC₁₋₄alkoxycarbonylamino;

and wherein when R¹² is substituted C₃₋₈cycloalkyl,C₃₋₈cycloalkylC₁₋₆alkyl, heterocyclyl, or heterocyclylC₁₋₆alkyl, R¹³ mayalso represent oxo on the C₃₋₈cycloalkyl or heterocyclyl moiety;

or

R⁸ represents —NR¹⁴R¹⁵, wherein R¹⁴ is hydrogen, cyano, C₁₋₆alkyl,C₁₋₆alkoxy, C₂₋₆alkenyl, C₂₋₆alkynyl, C₃₋₆alkenyloxy, C₃₋₆alkynyloxy,cyanoC₁₋₆alkyl, C₁₋₆ haloalkyl, C₁₋₆ haloalkenyl, hydroxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₄ haloalkoxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl, aminoC₁₋₆alkyl,N—C₁₋₄alkylaminoC₁₋₆alkyl, N,N-diC₁₋₄alkylaminoC₁₋₆alkyl,C₁₋₆alkylcarbonylC₁₋₆alkyl, C₁₋₆alkylcarbonylC₂₋₆alkenyl,C₁₋₆alkoxycarbonylC₁₋₆alkyl, C₁₋₆alkylcarbonyloxyC₁₋₆alkyl,N—C₁₋₄alkylaminocarbonylC₁₋₆alkyl,N,N-diC₁₋₄alkylaminocarbonylC₁₋₆alkyl, C₁₋₆alkylsulfonylC₁₋₆alkyl orC₁₋₆alkylsulfonylaminoC₁₋₆alkyl; or

R¹⁴ is C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₆alkyl,C₃₋₈cycloalkylC₁₋₆alkoxy, C₃₋₆cycloalkyloxy, wherein the cycloalkylmoiety is optionally partially unsaturated, phenyl, phenylC₁₋₆alkyl,phenylC₁₋₆alkoxy, heteroaryl, heteroarylC₁₋₆alkyl, heteroarylC₁₋₆alkoxy,wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromaticring which comprises 1, 2, 3 or 4 heteroatoms individually selected fromN, O and S, heterocyclyl, heterocyclylC₁₋₆alkyl orheterocyclylC₁₋₆alkoxy wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S;

wherein for R¹⁴, any cycloalkyl, phenyl, heteroaryl, heterocyclyl moietyis optionally substituted by 1, 2 or 3 substituents, which may be thesame or different, selected from R¹⁶; wherein

R¹⁶ is cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl,C₁₋₄ haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₂alkoxyC₁₋₂alkyl, C₁₋₄haloalkoxy, C₃₋₄alkenyloxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino,N,N-diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl,carbonylamino, N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyland C₁₋₄alkoxycarbonylamino;

and wherein when R¹⁴ is substituted C₃₋₈cycloalkyl,C₃₋₈cycloalkylC₁₋₆alkyl, C₃₋₈cycloalkylC₁₋₆alkoxy, heterocyclyl,heterocyclylC₁₋₆alkyl or heterocyclylC₁₋₆alkoxy, R¹⁶ may also representoxo on the C₃₋₈cycloalkyl or heterocyclyl moiety;

R¹⁵ is hydrogen, C₁₋₄alkyl, C₃₋₄alkynyl, C₁₋₄alkoxyC₁₋₄alkyl,cyanoC₁₋₄alkyl, C₃₋₆cycloalkyl, C₃₋₆cycloalkylC₁₋₂alkyl; or

R¹⁴ and R¹⁵, together with the nitrogen atom to which they are bonded,form a 4-, 5- or 6-membered cycle optionally containing an additionalheteroatom or group selected from O, S, S(O)₂, oxo (═O) and NR¹⁷;wherein

R¹⁷ is hydrogen, methyl, methoxy, formyl or acyl; or

a salt or an N-oxide thereof.

Surprisingly, it has been found that the novel compounds of formula (I)have, for practical purposes, a very advantageous level of biologicalactivity for protecting plants against diseases that are caused byfungi.

According to a second aspect of the invention, there is provided anagrochemical composition comprising a fungicidally effective amount of acompound of formula (I). The composition may further comprise at leastone additional active ingredient and/or an agrochemically-acceptablediluent or carrier.

According to a third aspect of the invention, there is provided a methodof controlling or preventing infestation of useful plants byphytopathogenic microorganisms, wherein a fungicidally effective amountof a compound of formula (I), or a composition comprising this compoundas active ingredient, is applied to the plants, to parts thereof or thelocus thereof.

According to a fourth aspect of the invention, there is provided the useof a compound of formula (I) as a fungicide. According to thisparticular aspect of the invention, the use may or may not includemethods for the treatment of the human or animal body by surgery ortherapy.

As used herein, the term “halogen” or “halo” refers to fluorine(fluoro), chlorine (chloro), bromine (bromo) or iodine (iodo),preferably fluorine, chlorine or bromine.

As used herein, cyano means a —CN group.

As used herein, amino means an —NH₂ group.

As used herein, hydroxy means an —OH group.

As used herein, carbonylamino means an —N(H)C(O)H group.

As used herein, formyl means an —C(O)H group.

As used herein, acyl means an —C(O)CH₃ group.

As used herein, the term “C₁₋₆alkyl” refers to a straight or branchedhydrocarbon chain radical consisting solely of carbon and hydrogenatoms, containing no unsaturation, having from one to six carbon atoms,and which is attached to the rest of the molecule by a single bond. Theterms “C₁₋₄alkyl” and “C₁₋₂alkyl” are to be construed accordingly.Examples of C₁₋₆alkyl include, but are not limited to, methyl, ethyl,n-propyl, 1-methylethyl (iso-propyl), n-butyl,1,1-dimethylethyl(tert-butyl) and n-pentyl. A “C₁-C₆alkylene” group refers to thecorresponding definition of C₁-C₆alkyl (and C₁₋₄alkyl and C₁₋₂alkyl),except that such radical is attached to the rest of the molecule by twosingle bonds. Examples of C₁-C₆alkylene, include, but are not limitedto, —CH₂—, —CH₂CH₂— and —(CH₂)₃—.

As used herein, the term “C₂₋₆alkenyl” refers to a straight or branchedhydrocarbon chain radical group consisting solely of carbon and hydrogenatoms, containing at least one double bond that can be of either the(E)- or (Z)-configuration, having from two to six carbon atoms, which isattached to the rest of the molecule by a single bond. The term“C₃₋₆alkenyl” is to be construed accordingly. Examples of C₂₋₆alkenylinclude, but are not limited to, ethenyl, prop-1-enyl, but-1-enyl.

As used herein, the term “C₂₋₆alkynyl” refers to a straight or branchedhydrocarbon chain radical group consisting solely of carbon and hydrogenatoms, containing at least one triple bond, having from two to sixcarbon atoms, and which is attached to the rest of the molecule by asingle bond. The term “C₃₋₄alkynyl” is to be construed accordingly.Examples of C₂₋₆alkynyl include, but are not limited to, ethynyl,prop-1-ynyl, but-1-ynyl.

As used herein, oxo means an ═O group, eg, a ketonyl (—C(O)—), sulfinyl(—S(O)—) or sulfonyl (—S(O)₂—) oxygen.

As used herein, the term “N—C₁₋₄alkylamino” refers to a radical of theformula —NH—R_(a) where R_(a) is a C₁₋₄alkyl radical as defined above.

As used herein, the term “N,N-diC₁₋₄alkylamino” refers to a radical ofthe formula —N(R_(a))—R_(a) where each R_(a) is a C₁₋₄alkyl radical,which may be the same or different, as defined above.

As used herein, the term “C₁₋₆alkoxy” refers to a radical of the formula—OR_(a) where R_(a) is a C₁₋₆alkyl radical as generally defined above.The terms “C₁₋₄alkoxy” and “C₁₋₂alkoxy” are to be construed accordingly.Examples of C₁₋₆alkoxy include, but are not limited to, methoxy, ethoxy,propoxy, iso-propoxy, butoxy.

As used herein, the term “C₁₋₄alkoxycarbonyloxy” refers to a radical ofthe formula —OC(O)R_(a) where R_(a) is a C₁₋₄alkoxy radical as generallydefined above.

As used herein, the term “C₁₋₄alkoxycarbonyloxyC₁₋₄alkyl” refers to aC₁₋₄alkyl radical as generally defined above substituted by aC₁₋₄alkoxycarbonyloxy radical as generally defined above.

As used herein, the term “hydroxyC₁₋₄alkyl” refers to a C₁₋₄alkylradical as generally defined above substituted by one or more hydroxygroups as defined above.

As used herein, the term “C₁₋₆alkylcarbonyl” refers to a radical of theformula —C(O)R_(a) where R_(a) is a C₁₋₆alkyl radical as generallydefined above. The term “C₁₋₄alkylcarbonyl” is to be construedaccordingly.

As used herein, the term “C₁₋₆alkoxycarbonyl” refers to a radical of theformula —C(O)OR_(a) where R_(a) is a C₁₋₆alkyl radical as generallydefined above. The term “C₁₋₄alkoxycarbonyl” is to be construedaccordingly.

As used herein, the term “C₁₋₆alkylcarbonyloxy” refers to a radical ofthe formula —OC(O)R_(a) where R_(a) is a C₁₋₆alkyl radical as generallydefined above. The term “C₁₋₄alkylcarbonyloxy” is to be construedaccordingly.

As used herein, the term “N—C₁₋₄alkylaminocarbonyl” refers to a radicalof the formula —C(O)NHR_(a) where R_(a) is a C₁₋₄alkyl radical asgenerally defined above.

As used herein, the term “N,N-diC₁₋₄alkylaminocarbonyl” refers to aradical of the formula —C(O)NR_(a)(R_(a)) where each R_(a) is aC₁₋₄alkyl radical as generally defined above.

As used herein, the term “C₁₋₄alkylcarbonylamino” refers to a radical ofthe formula —NHC(O)R_(a) where R_(a) is a C₁₋₄alkyl radical as generallydefined above.

As used herein, the term “C₁₋₄alkylcarbonylaminoC₁₋₆alkyl” refers to aC₁₋₆alkyl radical as generally defined above substituted by aC₁₋₄alkylcarbonylamino group as defined above.

As used herein, the term “C₁₋₄alkoxycarbonylamino” refers to a radicalof the formula —NHC(O)OR_(a) where R_(a) is a C₁₋₄alkyl radical asgenerally defined above.

As used herein, the term “C₁₋₄alkoxycarbonylaminoC₁₋₆alkyl” refers to aC₁₋₆alkyl radical as generally defined above substituted by aC₁₋₄alkoxycarbonylamino group as defined above.

As used herein, the term “C₁₋₆alkylsulfanyl” refers to a radical of theformula —SR_(a) where R_(a) is a C₁₋₆alkyl radical as generally definedabove. The term “C₁₋₄alkylsulfanyl” is to be construed accordingly.

As used herein, the term “C₁₋₆alkylsulfinyl” refers to a radical of theformula —S(O)R_(a) where R_(a) is a C₁₋₆alkyl radical as generallydefined above. The term “C₁₋₄alkylsulfonyl” is to be construedaccordingly.

As used herein, the term “C₁₋₆alkylsulfonyl” refers to a radical of theformula —S(O)₂R_(a) where R_(a) is a C₁₋₆alkyl radical as generallydefined above. The term “C₁₋₄alkylsulfonyl” is to be construedaccordingly.

As used herein, the term “C₁₋₆alkylsulfonylamino” refers to a radical ofthe formula —NHS(O)₂R_(a) where R_(a) is a C₁₋₆alkyl radical asgenerally defined above. The term “C₁₋₄alkylsulfonylamino” is to beconstrued accordingly.

As used herein, the term “C₃₋₆alkenyloxy” refers to a radical of theformula —OR_(a) where R_(a) is a C₃₋₆alkenyl radical as generallydefined above.

As used herein, the term “C₂₋₆alkynloxy” refers to a radical of theformula —OR_(a) where R_(a) is a C₂₋₆alkynyl radical as generallydefined above. The terms “C₂₋₄alkynloxy” and “C₃₋₆alkynyloxy” are to beconstrued accordingly.

As used herein, the term “C₃₋₆ haloalkenyloxy” refers to aC₃₋₆alkenyloxy radical as generally defined above substituted by one ormore of the same or different halogen atoms.

As used herein, the term “C₂₋₆alkynyloxycarbonylamino” refers to aradical of the formula —NHC(O)OR_(a) where R_(a) is a C₂₋₆alkynylradical as generally defined above. The term“C₂₋₄alkynyloxycarbonylamino” is to be construed accordingly.

As used herein, the term “C₁₋₄ haloalkoxy” refers to a C₁₋₄alkoxy groupas defined above substituted by one or more of the same or differenthalogen atoms. Examples of C₁₋₄ haloalkoxy include, but are not limitedto, fluoromethoxy, fluoroethoxy, trifluoromethoxy, trifluoroethoxy.

As used herein, the term “cyanoC₁₋₆alkyl” refers to a C₁₋₆alkyl radicalas generally defined above substituted by one or more cyano groups asdefined above. The term “cyanoC₁₋₄alkyl” is to be construed accordingly.Examples of cyanoC₁₋₆alkyl include, but are not limited to cyanomethyl,cyanoethyl.

As used herein, the term “C₁₋₆ haloalkyl” refers to a C₁₋₆alkyl radicalas generally defined above substituted by one or more of the same ordifferent halogen atoms. The term “C₁₋₄ haloalkyl” is to be construedaccordingly. Examples of C₁₋₆ haloalkyl include, but are not limited tofluoromethyl, fluoroethyl, trifluoromethyl, 2,2,2-trifluoroethyl.

As used herein, the term “C₂₋₆ haloalkenyl” refers to a C₂₋₆alkenylradical as generally defined above substituted by one or more of thesame or different halogen atoms. The terms “C₂₋₄ haloalkenyl” and “C₃₋₆haloalkenyl” are to be construed accordingly.

As used herein, the term “C₁₋₄ haloalkylcarbonyloxy” refers to a radicalof the formula —OC(O)R_(a) where R_(a) is a C₁₋₄ haloalkyl radical asgenerally defined above.

As used herein, the term “C₁₋₄ haloalkylcarbonyloxyC₁₋₄alkyl” refers toa C₁₋₄alkyl radical as generally defined above substituted by a C₁₋₄haloalkylcarbonyloxy radical as generally defined above.

As used herein, the term “hydroxyC₁₋₆alkyl” refers to a C₁₋₆alkylradical as generally defined above substituted by one or more hydroxygroups as defined above. The term “hydroxyC₁₋₄alkyl” is to be construedaccordingly.

As used herein, the term “C₁₋₄alkoxyC₁₋₆alkyl” refers to a C₁₋₆alkylradical as generally defined above substituted by a C₁₋₄alkoxy group asdefined above. The terms “C₁₋₄alkoxyC₁₋₄alkyl” and “C₁₋₂alkoxyC₁₋₄alkyl”are to be construed accordingly. Examples of C₁₋₄alkoxyC₁₋₆alkylinclude, but are not limited to methoxymethyl, 2-methoxyethyl.

As used herein, the term “C₁₋₄ haloalkoxyC₁₋₆alkyl” refers to aC₁₋₆alkyl radical as generally defined above substituted by a C₁₋₄haloalkoxy group as defined above. The terms “C₁₋₄ halolalkoxyC₁₋₄alkyl”and “C₁₋₂ haloalkoxyC₁₋₄alkyl” are to be construed accordingly.

As used herein, the term “C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl” refers to aC₁₋₆alkyl radical as generally defined above substituted by a C₁₋₄alkoxygroup as defined above, the C₁₋₄alkoxy group itself substituted by aC₁₋₄alkoxy group as defined above.

As used herein, the term “C₂₋₆alkynyloxyC₁₋₆alkyl” refers to a C₁₋₆alkylradical as generally defined above substituted by a C₂₋₆alkynyloxy groupas defined above.

As used herein, the term “aminoC₁₋₆alkyl” refers to a C₁₋₆alkyl radicalas generally defined above substituted by one or more amino groups asdefined above. The term “aminoC₁₋₄alkyl” is to be construed accordingly.

As used herein, the term “N—C₁₋₄alkylaminoC₁₋₆alkyl” refers to aC₁₋₆alkyl radical as generally defined above substituted by aN—C₁₋₄alkylamino group as defined above. The term“N—C₁₋₄alkylaminoC₁₋₄alkyl” is to be construed accordingly.

As used herein, the term “N,N-diC₁₋₄alkylaminoC₁₋₆alkyl” refers to aC₁₋₆alkyl radical as generally defined above substituted by aN,N-diC₁₋₄alkylamino group as defined above. The term“N,N-diC₁₋₄alkylaminoC₁₋₄alkyl” is to be construed accordingly.

As used herein, the term “C₁₋₆alkylcarbonylC₁₋₆alkyl” refers to aC₁₋₆alkyl radical as generally defined above substituted by aC₁₋₆alkylcarbonyl group as defined above. The term“C₁₋₆alkylcarbonylC₁₋₄alkyl” is to be construed accordingly.

As used herein, the term “C₁₋₆alkylcarbonylC₂₋₆alkenyl” refers to aC₂₋₆alkenyl radical as generally defined above substituted by aC₁₋₆alkylcarbonyl group as defined above. The term“C₁₋₆alkylcarbonylC₂₋₄alkenyl” is to be construed accordingly.

As used herein, the term “C₁₋₆alkoxycarbonylC₁₋₆alkyl” refers to aC₁₋₆alkyl radical as generally defined above substituted by aC₁₋₆alkoxycarbonyl group as defined above. The term“C₁₋₆alkoxycarbonylC₁₋₄alkyl” is to be construed accordingly.

As used herein, the term “C₁₋₆alkylcarbonyloxyC₁₋₆alkyl” refers to aC₁₋₆alkyl radical as generally defined above substituted by aC₁₋₆alkylcarbonyloxy group as defined above. The term“C₁₋₆alkylcarbonyloxyC₁₋₄alkyl” is to be construed accordingly.

As used herein, the term “N—C₁₋₄alkylaminocarbonylC₁₋₆alkyl”, refers toa C₁₋₆alkyl radical as generally defined above substituted by aN—C₁₋₄alkylaminocarbonyl group as defined above. The term“N—C₁₋₄alkylaminocarbonylC₁₋₄alkyl” is to be construed accordingly.

As used herein, the term “N,N-diC₁₋₄alkylaminocarbonylC₁₋₆alkyl”, refersto a C₁₋₆alkyl radical as generally defined above substituted by aN,N-diC₁₋₄alkylaminocarbonylC₁₋₆alkyl group as defined above. The term“N,N-diC₁₋₄alkylaminocarbonylC₁₋₄alkyl” is to be construed accordingly.

As used herein, the term “C₁₋₆alkylsulfanylC₁₋₆alkyl”, refers to aC₁₋₆alkyl radical as generally defined above substituted by aC₁₋₆alkylsulfanyl group as defined above. The term“C₁₋₆alkylsulfanylC₁₋₄alkyl” is to be construed accordingly.

As used herein, the term “C₁₋₆alkylsulfonylC₁₋₆alkyl”, refers to aC₁₋₆alkyl radical as generally defined above substituted by aC₁₋₆alkylsulfonyl group as defined above. The term“C₁₋₆alkylsulfonylC₁₋₄alkyl” is to be construed accordingly.

As used herein, the term “C₁₋₆alkylsulfonylaminoC₁₋₆alkyl”, refers to aC₁₋₆alkyl radical as generally defined above substituted by aC₁₋₆alkylsulfonylamino group as defined above. The term“C₁₋₆alkylsulfonylaminoC₁₋₄alkyl” is to be construed accordingly.

As used herein, the term “C₁₋₆alkylsulfonylaminoC₂₋₆alkynyl”, refers toa C₂₋₆alkynyl radical as generally defined above substituted by aC₁₋₆alkylsulfonylamino group as defined above. The term“C₁₋₆alkylsulfonylaminoC₂₋₄alkynyl” is to be construed accordingly.

As used herein, C₂₋₆alkynyloxycarbonylaminoC₁₋₆alkyl refers to aC₁₋₆alkyl radical as generally defined above substituted by aC₂₋₆alkynyloxycarbonylamino group as defined above. The term“C₂₋₄alkynyloxycarbonylaminoC₁₋₄alkyl” is to be construed accordingly.

As used herein, the term “C₃₋₈cycloalkyl” may be mono- or bi-cyclic andcontains 3 to 8 carbon atoms. “C₃₋₆cycloalkyl” is to be construedaccordingly. Examples of C₃₋₈cycloalkyl include, but are not limited to,cyclopropyl, 1-methylcyclopropyl, 2-methylcyclopropyl, cyclobutyl,cyclopentyl and cyclohexyl.

As used herein, the term “aryl” refers to an aromatic ring systemconsisting solely of carbon and hydrogen atoms which may be mono-, bi-or tricyclic. Examples of such ring systems include phenyl,naphthalenyl, anthracenyl, indenyl or phenanthrenyl.

As used herein, the term “heteroaryl” refers to a 5- or 6-memberedaromatic monocyclic ring radical which comprises 1, 2, 3 or 4heteroatoms individually selected from nitrogen, oxygen and sulfur. Theheteroaryl radical may be bonded via a carbon atom or heteroatom.Examples of heteroaryl include, but are not limited to, furyl, pyrrolyl,thienyl, pyrazolyl, imidazolyl, thiazolyl, isothiazolyl, oxazolyl,isoxazolyl, triazolyl, tetrazolyl, pyrazinyl, pyridazinyl, pyrimidyl orpyridyl.

As used herein, the term “heterodiaryl” refers to a stable 9- or10-membered bicyclic aromatic ring system which comprises 1, 2, 3 or 4heteroatoms individually selected from nitrogen, oxygen and sulfur. Theheteroaryl radical may be bonded via a carbon atom or heteroatom.

As used herein, the term “heterocyclyl” or “heterocyclic” refers to astable 4-, 5- or 6-membered non-aromatic monocyclic ring radical whichcomprises 1, 2, or 3, heteroatoms individually selected from nitrogen,oxygen and sulfur. The heterocyclyl radical may be bonded to the rest ofthe molecule via a carbon atom or heteroatom. Examples of heterocyclylinclude, but are not limited to, azetidinyl, oxetanyl, pyrrolinyl,pyrrolidyl, thietanyl, tetrahydrofuryl, tetrahydrothienyl,tetrahydrothiopyranyl, piperidyl, piperazinyl, tetrahydropyranyl,morpholinyl or perhydroazepinyl.

As used herein, the term “C₃₋₈cycloalkylC₀₋₆alkyl” refers to aC₃₋₈cycloalkyl ring as defined above attached to the rest of themolecule by a single bond or by a C₁-C₆alkylene radical as definedabove. “C₃₋₆cycloalkylC₁₋₂alkyl” is to be construed accordingly.Examples of C₃₋₈cycloalkylC₀₋₆alkyl include, but are not limited to,cyclopropyl, cyclopropylmethyl, cyclopropylethyl, cyclobutyl,cyclopentyl or cyclohexyl.

As used herein, the term “C₃₋₆cycloalkylC₁₋₂alkoxy” refers to aC₁₋₂alkoxy radical as generally defined above substituted by aC₃₋₆cycloalkyl ring as defined above.

As used herein, the term “C₃₋₆cycloalkylcarbonyl” refers to a —C(O)R^(a)radical, wherein R^(a) is a C₃₋₆cycloalkyl ring as defined above.

As used herein, the term “C₃₋₆cycloalkylcarbonyloxy” refers to a—OC(O)R^(a) radical wherein R^(a) is a C₃₋₆cycloalkyl ring as describedabove.

As used herein, the term “C₃₋₆cycloalkylcarbonyloxyC₁₋₄alkyl” refers toa C₃₋₆cycloalkylcarbonyloxy group as described above attached to therest of the molecule by a C₁₋₄alkylene radical as defined above.

As used herein, the term “phenylC₀₋₆alkyl” refers to a phenyl ringattached to the rest of the molecule by a single bond or by aC₁₋₆alkylene radical as defined above. “phenylC₁₋₆alkyl” and“phenylC₁₋₂alkyl” are to be construed accordingly. Examples ofphenylC₀₋₆alkyl include, but are not limited to, phenyl, benzyl or2-phenylethyl.

As used herein, the term “phenylC₁₋₂alkoxy” refers to a C₁₋₂alkoxyradical as generally defined above substituted by a phenyl ring.

As used herein, the term “phenylC₂₋₆alkenyl” refers to a C₂₋₆alkenylradical as generally defined above substituted by a phenyl ring.

As used herein, the term “phenylcarbonyloxy” refers to a —OC(O)R^(a)radical wherein R^(a) is a phenyl ring.

As used herein, the term “phenylcarbonyloxyC₁₋₄alkyl” refers to aphenylcarbonyloxy group as described above attached to the rest of themolecule by a C₁₋₄alkylene radical as defined above.

As used herein, the term “naphthylC₀₋₆alkyl” refers to a naphthalenering attached to the rest of the molecule by a single bond or by aC₁₋₆alkylene radical as defined above.

As used herein, the term “heteroarylC₀₋₆alkyl” refers to a heteroarylring as described above attached to the rest of the molecule by a singlebond or by a C₁₋₆alkylene radical as defined above.“HeteroarylC₁₋₆alkyl” and “heteroarylC₁₋₂alkyl” are to be construedaccordingly.

As used herein, the term “heteroarylC₁₋₆alkoxy” refers to a C₁₋₆alkoxyradical as generally defined above substituted by a heteroaryl group asgenerally defined above. HeteroarylC₁₋₂alkoxy″ is to be construedaccordingly.

As used herein, the term “heterodiarylC₀₋₆ alkyl” refers to aheterodiaryl ring as described above attached to the rest of themolecule by a single bond or by a C₁₋₆alkylene radical as defined above.“HeterodiarylC₁₋₆alkyl” and “heterodiarylC₁₋₂alkyl” are to be construedaccordingly.

As used herein, the term “heterocyclylC₀₋₆alkyl” refers to aheterocyclyl ring as described above attached to the rest of themolecule by a single bond or by a C₁₋₆alkylene radical as defined above.“HeterocyclylC₁₋₆alkyl” and “heterocyclylC₁₋₂alkyl” are to be construedaccordingly.

As used herein, the term “heterocyclylC₁₋₆alkoxy” refers to a C₁₋₆alkoxyradical as generally defined above substituted by a heterocyclyl groupas generally defined above. “HeterocyclylC₁₋₂alkoxy” is to be construedaccordingly.

As used herein, the term “heterocyclylcarbonyloxy” refers to a—OC(O)R^(a) radical wherein R^(a) is a heteroaryl ring as describedabove.

As used herein, the term “heterocyclylcarbonyloxyC₁₋₄alkyl” refers to aheterocyclylcarbonyloxy group as described above attached to the rest ofthe molecule by a C₁₋₄alkylene radical as defined above.

As used herein, the term “C₃₋₆cycloalkylcarbonylaminoC₁₋₆alkyl” refersto a a radical of the formula —R_(a)NHC(O)R_(b), wherein R_(a) is aC₁₋₆alkyl radical as defined above and R_(b) is a C₃₋₆cycloalkyl ring asdescribed above.

The presence of one or more possible asymmetric carbon atoms in acompound of formula (I) means that the compounds may occur in chiralisomeric forms, i.e., enantiomeric or diastereomeric forms. Alsoatropisomers may occur as a result of restricted rotation about a singlebond. Formula (I) is intended to include all those possible isomericforms and mixtures thereof. The present invention includes all thosepossible isomeric forms and mixtures thereof for a compound of formula(I). Likewise, formula (I) is intended to include all possible tautomers(including lactam-lactim tautomerism and keto-enol tautomerism) wherepresent. The present invention includes all possible tautomeric formsfor a compound of formula (I).

In each case, the compounds of formula (I) according to the inventionare in free form, in covalently hydrated form, in oxidized form as anN-oxide or in salt form, e.g., an agronomically usable or agrochemicallyacceptable salt form.

N-oxides are oxidized forms of tertiary amines or oxidized forms ofnitrogen containing heteroaromatic compounds. They are described forinstance in the book “Heterocyclic N-oxides” by A. Albini and S. Pietra,CRC Press, Boca Raton 1991.

The following list provides definitions, including preferreddefinitions, for substituents n, A¹, A², A³, A⁴, R¹, R², R³, R⁴, R⁵, R⁶,R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶ and R¹⁷ with reference tothe compounds of formula (I). For any one of these substituents, any ofthe definitions given below may be combined with any definition of anyother substituent given below or elsewhere in this document.

n represents 1 or 2. In some embodiments of the invention, n is 1, Inother embodiments of the invention, n is 2. Preferably, n is 1.

A¹ represents N or CR¹, wherein R¹ is hydrogen, halogen, methyl, ethyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy.

A² represents N or CR², wherein R² is hydrogen, halogen, methyl, ethyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy.

A³ represents N or CR³, wherein R³ is hydrogen or halogen.

A⁴ represents N or CR⁴, wherein R⁴ is hydrogen or halogen. and

wherein 0, 1 or 2 of A¹, A², A³ and A⁴ are N;

R¹ and R² are independently selected from hydrogen, halogen, methyl,ethyl. difluoromethyl, trifluoromethyl, methoxy, ethoxy, ordifluoromethoxy. Preferably, R¹ and R² are independently selected fromhydrogen and halogen. More preferably, R¹ and R² are hydrogen.

R³ and R⁴ are independently selected from hydrogen and halogen.Preferably, R³ and R⁴ are independently selected from hydrogen andfluoro. More preferably, R³ and R⁴ are hydrogen.

A³ may represent CR³, wherein R³ is hydrogen or halogen.

A⁴ may represent CR⁴, wherein R⁴ is hydrogen or halogen.

In the compounds according to Formula (I), at least two of R¹, R², R³and R⁴ may be hydrogen. Preferably, three of R¹, R², R³ and R⁴ may behydrogen, wherein more preferably R², R³ and R⁴ are hydrogen.

In some embodiments of the invention, the 6-membered ring comprising A¹to A⁴ is a phenyl (where A¹ to A⁴ are C—H), pyridinyl (where A¹ or A³ isN and the other A positions are C—H), pyrimidinyl (where A¹ and A³ are Nand the other A positions are C—H), fluorophenyl (where A¹ or A³ are C—F(preferably A³ is C—F) and the other A positions are C—H) ordifluorophenyl (where A¹ and A³ are C—F and the A² and A⁴ positions areC—H) group.

In the compounds according to Formula (I), when R⁸ is not —OR¹² or—NR¹⁴R¹⁵, preferably A¹, A², A³ and A⁴ are C—H; A², A³ and A⁴ are C—Hand A¹ is N; A¹, A² and A⁴ are C—H and A³ is N; A¹, A² and A⁴ are C—Hand A³ is C-halogen (preferably fluoro); A², A³ and A⁴ are C—H and A¹ isC-halogen (preferably fluoro) or A², A³ and A⁴ are C—H and A¹ isC-halogen (preferably fluoro); A² and A⁴ are C—H and A¹ and A³ areC-halogen (preferably fluoro); or A³ and A⁴ are C—H and A¹ and A² areC-halogen (preferably fluoro). More preferably, A¹, A², A³, and A⁴ areC—H.

In the compounds according to Formula (I), when R⁸ is —OR¹², preferablyA¹, A², A³ and A⁴ are C—H.

In the compounds according to Formula (I), when R⁸ is —NR¹⁴R¹⁵,preferably A¹, A², A³ and A⁴ are C—H; A¹, A² and A⁴ are C—H and A³ isC-halogen (preferably fluoro); or A², A³ and A⁴ are C—H and A¹ isC-halogen (preferably fluoro). More preferably, A¹, A², A³ and A⁴ areC—H.

R⁵ and R⁶ independently represent hydrogen, C₁₋₄alkyl, halogen, cyano,trifluoromethyl and difluoromethyl, or R⁵ and R⁶ together with thecarbon atom they share form a cyclopropyl. Preferably, R⁵ and R⁶ may beindependently selected from hydrogen, C₁₋₄alkyl, halogen, cyano,trifluoromethyl and difluoromethyl, or R⁵ and R⁶ together with thecarbon atom they share form a cyclopropyl. More preferably, R⁵ and R⁶are independently selected from hydrogen, C₁₋₄alkyl (in particularmethyl) and cyano.

In the compounds according to Formula (I), when R⁸ is not —OR or—NR¹⁴R¹⁵, preferably R⁵ and R⁶ are hydrogen; R⁵ is hydrogen and R⁶ ismethyl; or R⁵ is hydrogen and R⁶ is cyano. More preferably, R⁵ and R⁶are hydrogen and n is 1.

In the compounds according to Formula (I), when R⁸ is —OR¹², preferablyR⁵ and R⁶ are hydrogen and n is 1.

In the compounds according to Formula (I), when R⁸ is —NR¹⁴R¹⁵,preferably R⁵ and R⁶ are hydrogen and n is 1.

R⁷ is hydroxy, C₁₋₄alkyl, C₂₋₄ haloalkyl, C₁₋₄alkoxy, hydroxyC₁₋₄alkyl,C₁₋₂alkoxyC₁₋₄alkyl, C₁₋₂haloalkoxyC₁₋₄alkyl, C₃₋₄alkynyl, C₃₋₆alkenyl,C₃₋₆alkenyloxy, C₃₋₆alkynyloxy, C₃₋₆ haloalkenyl, C₃₋₆haloalkenyloxy,C₁₋₄alkylcarbonyloxy, C₁₋₄ haloalkylcarbonyloxy, C₁₋₄alkoxycarbonyloxy,C₁₋₄alkylcarbonyloxyC₁₋₄alkyl, C₁₋₄ haloalkylcarbonyloxyC₁alkyl,C₁₋₄alkoxycarbonyloxyC₁₋₄alkyl; or R⁷ is C₃₋₆cycloalkyl,C₃₋₆cycloalkylC₁₋₂alkyl, C₃₋₆cycloalkylC₁₋₂alkoxy, phenyl,phenylC₁₋₂alkyl, phenylC₁₋₂alkoxy, heteroaryl, heteroarylC₁₋₂alkyl,heteroarylC₁₋₂alkoxy, heterocyclyl, heterocyclylC₁₋₂alkyl,heterocyclylC₁₋₂alkoxy, C₃₋₆cycloalkylcarbonyloxy,heterocyclylcarbonyloxy, phenylcarbonyloxy,C₃₋₆cycloalkylcarbonyloxyC₁₋₄alkyl, heterocyclylcarbonyloxyC₁₋₄alkyl orphenylcarbonyloxyC₁₋₄alkyl; wherein the heteroaryl moiety is a 5- or6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, the heterocyclylmoiety is a 4- to 6-membered non-aromatic ring which comprises 1 or 2heteroatoms individually selected from N, O and S, and wherein any ofsaid cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties areoptionally substituted by 1 or 2 substituents selected from cyano,fluoro, chloro, bromo, methyl, difluoromethyl, trifluoromethyl, methoxy,ethoxy, or difluoromethoxy.

Preferably, R⁷ is C₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₂alkoxyC₁₋₄alkyl, C₁₋₂haloalkoxyC₁₋₄alkyl, C₃₋₆alkenyl, C₃₋₄alkynyl, C₃₋₆alkenyloxy,C₃₋₆alkynyloxy, C₃₋₆ haloalkenyl, C₃₋₆ haloalkenyloxy, C₃₋₆cycloalkyl,C₃₋₆cycloalkylC₁₋₂alkyl, C₃₋₆cycloalkylC₁₋₂alkoxy, phenyl,phenylC₁₋₂alkyl, phenylC₁₋₂alkoxy, heteroaryl, heteroarylC₁₋₂alkyl,heteroarylC₁₋₂alkoxy, heterocyclyl, heterocyclylC₁₋₂alkyl, orheterocyclylC₁₋₂alkoxy.

More preferably, R⁷ is C₁₋₄alkyl, C₁₋₄alkoxy, C₁₋₂alkoxyC₁₋₄alkyl,C₃₋₆alkenyl, C₃₋₄alkynyl, C₃₋₆alkenyloxy, C₃₋₆ haloalkenyl, C₃₋₆haloalkenyloxy, C₃₋₆cycloalkyl, C₃₋₆cycloalkylC₁₋₂alkyl,phenylC₁₋₂alkoxy, heteroarylC₁₋₂alkyl, or heterocyclylC₁₋₂alkyl.

In the compounds according to Formula (I), when R⁸ is not —OR¹² or—NR¹⁴R¹⁵, preferably R⁷ is hydroxy, C₁₋₄alkyl, C₂₋₄ haloalkyl,C₁₋₄alkoxy, hydroxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₄alkyl, C₃₋₆alkenyl,C₃₋₄alkynyl, C₃₋₆ haloalkenyloxy, C₃₋₆cycloalkyl,C₃₋₆cycloalkylC₁₋₂alkyl, phenylC₁₋₂alkoxy, heterocyclyl,heterocyclylC₁₋₂alkyl, heteroaryl or heteroarylC₁₋₂alkyl, wherein theheteroaryl moiety is a 5-membered monocyclic aromatic ring whichcomprises 1 or 2 heteroatoms individually selected from N, O and S, theheterocyclyl moiety is a 5-membered non-aromatic ring which comprises 1or 2 heteroatoms individually selected from N, O and S, and wherein anyof said cycloalkyl, phenyl, heteroaryl and heterocyclyl moieties areoptionally substituted by 1 or 2 substituents selected from cyano,fluoro, chloro, bromo, methyl, difluoromethyl, trifluoromethyl, methoxy,ethoxy, or difluoromethoxy. More preferably, R⁷ is hydroxy, C₁₋₄alkyl,C₂₋₄fluoroalkyl, C₁₋₄alkoxy, hydroxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₄alkyl,C₃₋₄alkenyl, C₃₋₄alkynyl, C₃₋₆ haloalkenyloxy, cyclopropyl,(cyclopropyl)methyl, phenylC₁₋₂alkoxy, (tetrahydrofuran-2-yl)methyl or(2-furyl)methyl, wherein any of said cyclopropyl, phenyl,tetrahydrofuran-2-yl and 2-furyl moieties are optionally substituted by1 or 2 substituents selected from cyano, fluoro, chloro, bromo, methyl,difluoromethyl, trifluoromethyl, methoxy, ethoxy, or difluoromethoxy.

In the compounds according to Formula (I), when R⁸ is not —OR¹² or—NR¹⁴R¹⁵, still more preferably R⁷ is C₁₋₄alkyl, C₂₋₄ haloalkyl,C₁₋₄alkoxy or C₃₋₆cycloalkyl. Further more preferably, R⁷ is C₁₋₄alkyl,C₂₋₄fluoroalkyl, methoxy, ethoxy or cyclopropyl. Most preferably, R⁷ ismethyl, ethyl, n-propyl, iso-propyl, 2,2,2-fluoroethyl, methoxy, ethoxyor cyclopropyl.

In the compounds according to Formula (I), when R⁸ is —OR¹², preferablyR⁷ is hydroxy, C₁₋₄alkyl, C₂₋₄ haloalkyl, C₁₋₄alkoxy, C₃₋₆alkenyl,C₃₋₄alkynyl, C₁₋₄alkoxycarbonyloxy. More preferably, R⁷ is hydroxy,C₁₋₄alkyl, C₂₋₄ haloalkyl, C₁₋₄alkoxy, C₃₋₄alkenyl, C₃₋₄alkynyl,C₁₋₄alkoxycarbonyloxy. Even more preferably, R⁷ is C₁₋₄alkoxy, inparticular, methoxy.

In the compounds according to Formula (I), when R⁸ is —NR¹⁴R¹⁵,preferably R⁷ is hydroxy, C₁₋₄alkyl, C₂₋₄ haloalkyl, C₁₋₄alkoxy,C₃₋₆alkenyl, C₃₋₄alkynyl, C₃₋₆cycloalkyl. More preferably, R⁷ ishydroxy, C₁₋₄alkyl, C₂ haloalkyl, C₁₋₂alkoxy, C₃₋₄alkenyl, C₃₋₄alkynyl,cyclopropyl. Even more preferably, R⁷ is C₁₋₄alkyl or C₁₋₄alkoxy, and inparticular, methyl, ethyl or methoxy.

R⁸ is hydrogen, C₁₋₆alkyl, C₂₋₆alkenyl, C₂₋₆alkynyl, cyanoC₁₋₆alkyl,C₁₋₆haloalkyl, C₂₋₆haloalkenyl, hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl,C₁₋₄ haloalkoxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl,C₂₋₄alkynyloxyC₁₋₆alkyl, aminoC₁₋₆alkyl, N—C₁₋₄alkylaminoC₁₋₆alkyl,N,N-diC₁₋₄alkylaminoC₁₋₆alkyl, C₁₋₆alkylcarbonylC₁₋₆alkyl,C₁₋₆alkylcarbonylC₂₋₆alkenyl, C₁₋₆alkoxycarbonylC₁₋₆alkyl,C₁₋₆alkylcarbonyloxyC₁₋₆alkyl, N—C₁₋₄alkylaminocarbonylC₁₋₆alkyl,N,N-diC₁₋₄alkylaminocarbonylC₁₋₆alkyl, C₁₋₆alkylsulfanylC₁₋₆alkyl,C₁₋₆alkylsulfonylC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₁₋₆alkyl,C₁₋₆alkylsulfonylaminoC₂₋₆alkynyl, C₂₋₆alkynyloxycarbonylaminoC₁₋₆alkyl,C₁₋₄alkylcarbonylaminoC₁₋₆alkyl, C₁₋₄alkoxycarbonylaminoC₁₋₆alkyl; or

R⁸ is C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₆alkyl, wherein the cycloalkylmoiety is optionally partially unsaturated, phenyl, phenylC₁₋₆alkyl,phenylC₂₋₆alkenyl, napthyl, naphthylC₁₋₆alkyl, heteroaryl,heteroarylC₁₋₆alkyl, wherein the heteroaryl moiety is a 5- or 6-memberedmonocyclic aromatic ring which comprises 1, 2, 3 or 4 heteroatomsindividually selected from N, O and S, heterodiaryl,heterodiarylC₁₋₆alkyl wherein the heterodiaryl moiety is a 9- or10-membered bicyclic aromatic system which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, heterocyclyl,heterocyclylC₁₋₆alkyl wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, orC₃₋₆cycloalkylcarbonylaminoC₁₋₆alkyl,

wherein for R⁸, any cycloalkyl, phenyl, napthyl, heteroaryl,heterodiaryl, heterocyclyl moiety is optionally substituted by 1, 2 or 3substituents, which may be the same or different, selected from R⁹; or,additionally, when R⁸ is cyclopropyl, the cyclopropyl moiety issubstituted by 4 substituents, which may be the same or different,selected from R⁹, with the proviso that at least 2 R⁹ substituents arethe same; wherein

R⁹ is cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl, C₁₋₄haloalkyl, C₂₋₄ haloalkenyl, C₁₋₄alkoxy, C₁₋₄ haloalkoxy,C₃₋₄alkynyloxy, N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino,C₁₋₄alkylcarbonyl, C₃₋₆cycloalkylcarbonyl, C₁₋₄alkoxycarbonyl,carbonylamino, N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl orC₁₋₄alkoxycarbonylamino, and wherein when R₈ is substitutedC₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₆alkyl, heterocyclyl, orheterocyclylC₁₋₆alkyl, R⁹ may also represent oxo on the C₃₋₈cycloalkylor heterocyclyl moiety; or

wherein for R⁸, any cycloalkyl, phenyl, napthyl, heteroaryl,heterodiaryl, heterocyclyl, moiety is optionally substituted by 1substituent selected from R¹⁰ and further optionally substituted by 1 or2 substituents selected from R⁹; wherein

R¹⁰ is C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₂alkyl, phenyl, phenylC₁₋₂alkyl,heteroaryl, heteroarylC₁₋₂alkyl wherein the heteroaryl moiety is a 5- or6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, heterocyclyl,heterocyclylC₁₋₆alkyl wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein any of saidcycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R¹¹; wherein

R¹¹ is hydrogen, cyano, fluoro, chloro, bromo, methyl, trifluoromethyl,methoxy and ethoxy.

In some embodiments of the compounds according to Formula (I), R⁸ ishydrogen, C₁₋₆alkyl, C₂₋₆alkenyl, C₂₋₆alkynyl, cyanoC₁₋₆alkyl, C₁₋₆haloalkyl, C₁₋₆ haloalkenyl, hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₄haloalkoxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl,C₂₋₄alkynyloxyC₁₋₆alkyl, aminoC₁₋₆alkyl, N—C₁₋₄alkylaminoC₁₋₆alkyl,N,N-diC₁₋₄alkylaminoC₁₋₆alkyl, C₁₋₆alkylcarbonylC₁₋₆alkyl,C₁₋₆alkylcarbonylC₂₋₆alkenyl, C₁₋₆alkoxycarbonylC₁₋₆alkyl,C₁₋₆alkylcarbonyloxyC₁₋₆alkyl, N—C₁₋₄alkylaminocarbonylC₁₋₆alkyl,N,N-diC₁₋₄alkylaminocarbonylC₁₋₆alkyl, C₁₋₆alkylsulfanylC₁₋₆alkyl,C₁₋₆alkylsulfonylC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₁₋₆alkyl,C₁₋₆alkylsulfonylaminoC₂₋₆alkynyl, orC₂₋₆alkynyloxycarbonylaminoC₁₋₆alkyl.

In some embodiments of the compounds according to Formula (I), R⁸ isC₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₆alkyl, wherein the cycloalkyl moietyis optionally partially unsaturated, phenyl, phenylC₁₋₆alkyl,phenylC₂₋₆alkenyl, napthyl, naphthylC₁₋₆alkyl, heteroaryl,heteroarylC₁₋₆alkyl, wherein the heteroaryl moiety is a 5- or 6-memberedmonocyclic aromatic ring which comprises 1, 2, 3 or 4 heteroatomsindividually selected from N, O and S, heterodiaryl,heterodiarylC₁₋₆alkyl wherein the heterodiaryl moiety is a 9- or10-membered bicyclic aromatic system which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, heterocyclyl,heterocyclylC₁₋₆alkyl wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, andC₃₋₆cycloalkylcarbonylaminoC₁₋₆alkyl. At least one of C₃₋₈cycloalkyl,C₃₋₈cycloalkylC₁₋₆alkyl, phenyl, phenylC₁₋₆alkyl, phenylC₂₋₆alkenyl,napthyl, naphthylC₁₋₆alkyl, heteroaryl, heteroarylC₁₋₆alkyl,heterodiaryl, heterodiarylC₁₋₆alkyl, heterocyclyl, heterocyclylC₁₋₆alkyland C₃₋₆cycloalkylcarbonylaminoC₁₋₆alkyl moieties may be substituted by1, 2 or 3 substituents selected from cyano, halogen, hydroxy, C₁₋₄alkyl,C₂₋₄alkenyl, C₂₋₄alkynyl, C₁₋₄ haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy,C₁₋₄ haloalkoxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino,C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, carbonylamino,N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl andC₁₋₄alkoxycarbonylamino.

Preferably, R⁸ is hydrogen, C₁₋₆alkyl, C₂₋₆alkenyl, C₂₋₆alkynyl,cyanoC₁₋₆alkyl, C₁₋₆ haloalkyl, C₂₋₆haloalkenyl, hydroxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₄ haloalkoxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl, C₂₋₄alkynyloxyC₁₋₆alkyl, aminoC₁₋₆alkyl,C₁₋₆alkylcarbonylC₁₋₆alkyl, C₁₋₆alkylcarbonylC₂₋₆alkenyl,C₁₋₆alkylcarbonyloxyC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₂₋₆alkynyl,C₂₋₆alkynyloxycarbonylaminoC₁₋₆alkyl, C₁₋₄alkylcarbonylaminoC₁₋₆alkyl,C₁₋₄alkoxycarbonylaminoC₁₋₆alkyl; or R⁸ is C₃₋₈cycloalkyl,C₃₋₈cycloalkylC₁₋₆alkyl, wherein the cycloalkyl moiety is optionallypartially unsaturated, phenyl, phenylC₁₋₆alkyl, phenylC₂₋₆alkenyl,napthyl, heteroaryl, heteroarylC₁₋₆alkyl, wherein the heteroaryl moietyis a 5- or 6-membered monocyclic aromatic ring which comprises 1, 2, 3or 4 heteroatoms individually selected from N, O and S, heterocyclyl,heterocyclylC₁₋₆alkyl wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, orC₃₋₆cycloalkylcarbonylaminoC₁₋₆alkyl, wherein for R⁸, any ofC₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₆alkyl, phenyl, phenylC₁₋₆alkyl,phenylC₂₋₆alkenyl, napthyl, heteroaryl, heteroarylC₁₋₆alkyl,heterocyclyl and heterocyclylC₁₋₆alkyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R⁹; wherein R⁹ is cyano, halogen, hydroxy, C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₄ haloalkoxy, C₃₋₄alkynyloxy,C₁₋₄alkylcarbonyl, C₃₋₆cycloalkylcarbonyl, C₁₋₄alkoxycarbonyl,carbonylamino; or wherein for R⁸, any of C₃₋₈cycloalkyl, phenyl moietiesare optionally substituted by 1 substituent selected from R¹⁰ and arefurther optionally substituted by 1 or 2 substituents selected from R⁹;wherein R¹⁰ is phenyl, heteroaryl wherein the heteroaryl moiety is a 5-or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, and wherein any ofsaid phenyl and heteroaryl moieties are optionally substituted by asingle substituents selected from R¹¹; wherein R¹¹ is cyano, fluoro,chloro, bromo, methyl, trifluoromethyl, methoxy and ethoxy.

More preferably, R⁸ is C₁₋₆alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl,cyanoC₁₋₄alkyl, C₁₋₆ haloalkyl, C₂₋₄haloalkenyl, hydroxyC₁₋₄alkyl,C₁₋₂alkoxyC₁₋₄alkyl, C₁₋₂ haloalkoxyC₁₋₄alkyl,C₁₋₂alkoxyC₁₋₂alkoxyC₁₋₄alkyl, C₂₋₄alkynyloxyC₁₋₄alkyl, aminoC₁₋₄alkyl,C₁₋₄alkylcarbonylC₁₋₄alkyl, C₁₋₄alkylcarbonylC₂₋₄alkenyl,C₁₋₄alkylcarbonyloxyC₁₋₄alkyl, C₁₋₄alkylsulfonylaminoC₂₋₄alkynyl,C₂₋₄alkynyloxycarbonylaminoC₁₋₄alkyl, C₁₋₂alkylcarbonylaminoC₁₋₄alkyl,C₁₋₂alkoxycarbonylaminoC₁₋₄alkyl; or R⁸ is C₃₋₆cycloalkyl,C₃₋₆cycloalkylC₁₋₂alkyl, wherein the cycloalkyl moiety is optionallypartially unsaturated, phenyl, phenylC₁₋₄alkyl, phenylC₂₋₄alkenyl,napthyl, heteroaryl, heteroarylC₁₋₂alkyl, wherein the heteroaryl moietyis a 5- or 6-membered monocyclic aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S, heterocyclyl,heterocyclylC₁₋₂alkyl wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, orC₃₋₆cycloalkylcarbonylaminoC₁₋₄alkyl, wherein for R⁸, any ofC₃₋₆cycloalkyl, C₃₋₆cycloalkylC₁₋₂alkyl, phenyl, phenylC₁₋₂alkyl,phenylC₂₋₄alkenyl, napthyl, heteroaryl, heteroarylC₁₋₂alkyl,heterocyclyl and heterocyclylC₁₋₂alkyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R⁹; wherein R⁹ is cyano, halogen, hydroxy,C₁₋₄alkyl, C₁₋₄ haloalkyl, C₂₋₄ haloalkenyl, C₁₋₄alkoxy, C₁₋₄haloalkoxy, C₃₋₄alkynyloxy, C₁₋₄alkylcarbonyl, C₃₋₆cycloalkylcarbonyl,C₁₋₄alkoxycarbonyl, carbonylamino; or wherein for R⁸, any ofC₃₋₆cycloalkyl, phenyl moieties are optionally substituted by 1substituent selected from R¹⁰ and are further optionally substituted by1 or 2 substituents selected from R⁹; wherein R¹⁰ is phenyl, heteroarylwherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromaticring which comprises 1, 2, 3 or 4 heteroatoms individually selected fromN, O and S, and wherein any of said phenyl and heteroaryl moieties areoptionally substituted by a single substituents selected from R¹¹;wherein R¹¹ is cyano, fluoro, chloro, bromo, methyl, trifluoromethyl,methoxy and ethoxy.

Even more preferably, R⁸ is C₁₋₆alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl,cyanoC₁₋₄alkyl, C₁₋₆ haloalkyl, C₂₋₄haloalkenyl, hydroxyC₁₋₄alkyl,C₁₋₂alkoxyC₁₋₄alkyl, C₁₋₂ haloalkoxyC₁₋₄alkyl,C₁₋₂alkoxyC₁₋₂alkoxyC₁₋₄alkyl, aminoC₁₋₄alkyl,C₁₋₂alkylcarbonylC₁₋₄alkyl, C₁₋₄alkylcarbonylC₂₋₄alkenyl,C₁₋₄alkylcarbonyloxyC₁₋₄alkyl, C₁₋₄alkylsulfonylaminoC₂₋₄alkynyl,C₁₋₂alkylcarbonylaminoC₁₋₄alkyl, C₂₋₄alkynyloxycarbonylaminoC₁₋₄alkyl,C₁₋₂alkoxycarbonylaminoC₁₋₄alkyl; or

R⁸ is C₃₋₆cycloalkyl, C₃₋₆cycloalkylC₁₋₂alkyl, phenyl, phenylC₁₋₄alkyl,phenylC₂₋₄alkenyl, napthyl, a heteroaryl-containing moiety selected fromfuranyl (including furan-2-yl, furan-3-yl), pyrazolyl (includingpyrazol-1-yl, pyrazol-3-yl, pyrazol-4-yl, pyrazol-5-yl), imidazolyl(including imidazol-1-yl, imidazol-2-yl, imidazol-4-yl, imidazol-5-yl),triazolyl (including 1,2,3-triazol-1-yl), 1,2,3-benzothiadiazole,(pyridinyl)methyl (including pyridin-2-methyl, pyridin-3-methyl,pyridin-4-methyl), or a heterocyclyl-containing moiety selected fromoxetanyl (including oxetan-2-yl, oxetan-3-yl), pyrrolidinyl (includingpyrrolidin-2-yl, pyrrolidin-3-yl), azetidinyl (including azetidin-2-yl,azetidin-3-yl), tetrahydrofuranyl (including tetrahydrofuran-2-yl,tetrahydrofuran-3-yl), 1,3-dioxolanyl (including 1,3-dioxolan-2-yl),thietanyl (including thietan-2-yl, thietan-3-yl), 1-oxo-thietan-3-yl,1,1-dioxo-thietan-3-yl, tetrahydropyranyl (includingtetrahydropyran-2-yl, tetrahydropyran-3-yl, tetrahydropyran-4-yl),tetrahydrothiopyranyl (including tetrahydrothiopyran-2-yl,tetrahydrothiopyran-3-yl, tetrahydrothiopyran-4-yl),C₃₋₆cycloalkylcarbonylaminoC₁₋₄alkyl,

wherein the cycle of each heteroaryl-containing moiety orheterocyclyl-containing moiety is optionally substituted by 1 or 2 or 3substituents, which may be the same of different, selected from R⁹;wherein

R⁹ is cyano, methyl, chloro, fluoro, hydroxyl, methoxy, trifluoromethyl,C₂-haloalkenyl, methylcarbonyl, ethylcarbonyl, carbonylamino; or

wherein the cycle of each heteroaryl-containing moiety orheterocyclyl-containing moiety is optionally substituted by 1substituent selected from R¹⁰ and further optionally substituted by 1 or2 substituents selected from R⁹, wherein

R¹⁰ is phenyl or pyridinyl (including pyridin-2-yl), wherein phenyl orpyridinyl is optionally substituted by 1, 2 or 3 substituents, which maybe the same or different, selected from R¹¹; wherein

R¹¹ is fluoro, chloro, bromo and methoxy.

In some embodiments of the compounds according to Formula (I),preferably, R⁸ is C₁₋₆alkyl, C₁₋₂ haloalkyl, hydroxyC₁₋₆alkyl,C₁₋₂alkoxyC₁₋₄alkyl, C₃₋₆cycloalkyl or heterocyclyl, wherein theheterocyclyl moiety is a 4- or 5-membered non-aromatic ring whichcomprises 1 or 2 heteroatoms individually selected from N and O, whereinC₃₋₆cycloalkyl and heterocyclyl are optionally substituted by 1, 2 or 3substituents, which may be the same or different, selected from R⁹;wherein R⁹ is cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl,C₂₋₄alkynyl, C₁₋₄ haloalkyl or C₁₋₄alkoxy.

More preferably, R C₁₋₄alkyl, C₁₋₂ haloalkyl, hydroxyC₁₋₄alkyl,C₁₋₂alkoxyC₁₋₄alkyl, C₃₋₆cycloalkyl or heterocyclyl, wherein theheterocyclyl moiety is a 4- or 5-membered non-aromatic ring whichcomprises 1 or 2 heteroatoms which are oxygen, wherein C₃₋₆cycloalkyland heterocyclyl are optionally substituted by 1 or 2 substituents,which may be the same or different, selected from R⁹; wherein R⁹ iscyano, fluoro, chloro, hydroxy, methyl, ethyl, trifluoromethyl andmethoxy.

Even more preferably, R⁸ is C₁₋₄alkyl, C₁₋₂ haloalkyl, hydroxyC₁₋₄alkyl,C₁₋₂alkoxyC₁₋₂alkyl, C₃₋₆cycloalkyl or heterocyclyl, wherein theheterocyclyl moiety is a 4- or 5-membered non-aromatic ring whichcomprises 1 or 2 heteroatoms which are oxygen, wherein C₃₋₆cycloalkyland heterocyclyl are optionally substituted by 1 or 2 substituents,which may be the same or different, selected from R⁹; wherein R⁹ isfluoro, chloro, methyl.

Still more preferably, R⁹ is C₁₋₄alkyl(methyl, ethyl, n-propyl,iso-propyl, n-butyl, sec-butyl, iso-butyl, t-butyl),2,2,2-trifluoroethyl, hydroxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₂alkyl, cyclopropylor heterocyclyl, wherein the heterocyclyl moiety istetrahydrofuran-2-yl, oxetan-3-yl or 1,3-dioxolan-2-yl, whereincyclopropyl and heterocyclyl are each optionally substituted by 1 or 2substituents selected from R⁹, wherein R⁹ is fluoro, chloro, methyl.

R⁸ may represent —OR¹², wherein R¹² is hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl,C₃₋₆alkynyl, cyanoC₁₋₆alkyl, C₁₋₆ haloalkyl, C₃₋₆ haloalkenyl,hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₄ haloalkoxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl, aminoC₁₋₆alkyl,N—C₁₋₄alkylaminoC₁₋₆alkyl, N,N-diC₁₋₄alkylaminoC₁₋₆alkyl,C₁₋₆alkylcarbonylC₁₋₆alkyl, C₁₋₆alkylcarbonylC₂₋₆alkenyl,C₁₋₆alkoxycarbonylC₁₋₆alkyl, C₁₋₆alkylcarbonyloxyC₁₋₆alkyl,N—C₁₋₄alkylaminocarbonylC₁₋₆alkyl,N,N-diC₁₋₄alkylaminocarbonylC₁₋₆alkyl, C₁₋₄alkylsulfanylC₁₋₆alkyl,C₁₋₆alkylsulfonylC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₁₋₆alkyl; or

R¹² is C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₆alkyl, wherein the cycloalkylmoiety is optionally partially unsaturated, phenyl, phenylC₁₋₆alkyl,heteroaryl, heteroarylC₁₋₆alkyl, wherein the heteroaryl moiety is a 5-or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, heterocyclyl,heterocyclylC₁₋₆alkyl, wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S;

wherein for R¹², any cycloalkyl, phenyl, heteroaryl, heterocyclyl moietyis optionally substituted by 1, 2 or 3 substituents, which may be thesame or different, selected from R¹³; wherein

R¹³ is cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl,C₁₋₄ haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₄ haloalkoxy,C₃₋₄alkenyloxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino,C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, carbonylamino,N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl orC₁₋₄alkoxycarbonylamino;

and wherein when R¹² is substituted C₃₋₈cycloalkyl,C₃₋₈cycloalkylC₁₋₆alkyl, heterocyclyl, or heterocyclylC₁₋₆alkyl, R¹³ mayalso represent oxo on the C₃₋₈cycloalkyl or heterocyclyl moiety;

Preferably, R¹² is hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl, C₃₋₆alkynyl,cyanoC₁₋₆alkyl, C₁₋₆ haloalkyl, C₃₋₆haloalkenyl, hydroxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₄ haloalkoxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl, aminoC₁₋₆alkyl,N—C₁₋₄alkylaminoC₁₋₆alkyl, N,N-diC₁₋₄alkylaminoC₁₋₆alkyl,C₁₋₆alkylcarbonylC₁₋₆alkyl, C₁₋₆alkylcarbonylC₂₋₆alkenyl,C₁₋₆alkoxycarbonylC₁₋₆alkyl, C₁₋₆alkylcarbonyloxyC₁₋₆alkyl,N—C₁₋₄alkylaminocarbonylC₁₋₆alkyl,N,N-diC₁₋₄alkylaminocarbonylC₁₋₆alkyl, C₁₋₄alkylsulfanylC₁₋₆alkyl,C₁₋₆alkylsulfonylC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₁₋₆alkyl, phenyl,phenylC₁₋₆alkyl, C₃₋₈cycloalkyl or C₃₋₈cycloalkylC₁₋₆alkyl. Morepreferably, R¹² is hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl, C₃₋₆alkynyl, C₁₋₆haloalkyl, C₁₋₄alkoxyC₁₋₆alkyl, phenyl, phenylC₁₋₆alkyl. Even morepreferably, R¹² is C₁₋₆alkyl, C₃₋₄alkenyl, C₃₋₄alkynyl, C₁₋₄ haloalkyl,C₁₋₂alkoxyC₁₋₄alkyl, phenyl, phenylC₁₋₂alkyl. Still more preferably, R¹²is C₁₋₆alkyl, C₃₋₄alkenyl, C₃₋₄alkynyl, C₁₋₄fluoroalkyl,C₁₋₄chloroalkyl, C₁₋₂alkoxyC₁₋₂alkyl, phenyl, benzyl.

R⁸ represents —NR¹⁴R¹⁵, wherein R¹⁴ is hydrogen, cyano, C₁₋₆alkyl,C₁₋₆alkoxy, C₂₋₆alkenyl, C₂₋₆alkynyl, C₃₋₆alkenyloxy, C₃₋₆alkynyloxy,cyanoC₁₋₆alkyl, C₁₋₆ haloalkyl, C₁₋₆ haloalkenyl, hydroxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₄ haloalkoxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl, aminoC₁₋₆alkyl,N—C₁₋₄alkylaminoC₁₋₆alkyl, N,N-diC₁₋₄alkylaminoC₁₋₆alkyl,C₁₋₆alkylcarbonylC₁₋₆alkyl, C₁₋₆alkylcarbonylC₂₋₆alkenyl,C₁₋₆alkoxycarbonylC₁₋₆alkyl, C₁₋₆alkylcarbonyloxyC₁₋₆alkyl,N—C₁₋₄alkylaminocarbonylC₁₋₆alkyl,N,N-diC₁₋₄alkylaminocarbonylC₁₋₆alkyl, C₁₋₄alkylsulfanylC₁₋₆alkyl,C₁₋₆alkylsulfonylC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₁₋₆alkyl; or

R¹⁴ is C₃₋₈cycloalkyl, C₃₋₈cycloalkylC₁₋₆alkyl,C₃₋₈cycloalkylC₁₋₆alkoxy, C₃₋₆cycloalkyloxy, wherein the cycloalkylmoiety is optionally partially unsaturated, phenyl, phenylC₁₋₆alkyl,phenylC₁₋₆alkoxy, heteroaryl, heteroarylC₁₋₆alkyl, heteroarylC₁₋₆alkoxy,wherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromaticring which comprises 1, 2, 3 or 4 heteroatoms individually selected fromN, O and S, heterocyclyl, heterocyclylC₁₋₆alkyl, heterocyclylC₁₋₆alkoxywherein the heterocyclyl moiety is a 4- to 6-membered non-aromatic ringwhich comprises 1, 2 or 3 heteroatoms individually selected from N, Oand S;

wherein for R¹⁴, any cycloalkyl, phenyl, heteroaryl, heterocyclyl moietyis optionally substituted by 1, 2 or 3 substituents, which may be thesame or different, selected from R¹⁶; wherein

R¹⁶ is cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl,C₁₋₄ haloalkyl, C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₂alkoxyC₁₋₂alkyl, C₁₋₄haloalkoxy, C₃₋₄alkenyloxy, C₃₋₄alkynyloxy, N—C₁₋₄alkylamino,N,N-diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl,carbonylamino, N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl orC₁₋₄alkoxycarbonylamino;

and wherein when R¹⁴ is substituted C₃₋₈cycloalkyl,C₃₋₈cycloalkylC₁₋₆alkyl, C₃₋₈cycloalkylC₁₋₆alkoxy, heterocyclyl, orheterocyclylC₁₋₆alkyl, heterocyclylC₁₋₆alkoxy, R¹⁶ may also representoxo on 35 the C₃₋₈cycloalkyl or heterocyclyl moiety;

R¹⁵ is hydrogen, C₁₋₄alkyl, C₃₋₄alkynyl, C₁₋₄alkoxyC₁₋₄alkyl,cyanoC₁₋₄alkyl, C₃₋₆cycloalkyl, C₃₋₆cycloalkylC₁₋₂alkyl; or

R¹⁴ and R¹⁵, together with the nitrogen atom to which they are bonded,form a 4-, 5- or 6-membered cycle optionally containing an additionalheteroatom selected from 0, S and NR¹⁷; wherein

R¹⁷ is hydrogen, methyl, methoxy, formyl or acyl.

Preferably, R⁸ represents —NR¹⁴R¹⁵, wherein R¹⁴ is hydrogen, C₁₋₆alkyl,C₁₋₆alkoxy, C₂₋₆alkenyl, C₂₋₆alkynyl, cyanoC₁₋₆alkyl, C₁₋₆haloalkyl,C₁₋₆haloalkenyl, hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl,C₁₋₄haloalkoxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl, aminoC₁₋₆alkyl,N—C₁₋₄alkylaminoC₁₋₆alkyl, N,N-diC₁₋₄alkylaminoC₁₋₆alkyl,C₁₋₆alkylcarbonylC₁₋₆alkyl, C₁₋₆alkylcarbonylC₂₋₆alkenyl,C₁₋₆alkoxycarbonylC₁₋₆alkyl, C₁₋₆alkylcarbonyloxyC₁₋₆alkyl,N—C₁₋₄alkylaminocarbonylC₁₋₆alkyl,N,N-diC₁₋₄alkylaminocarbonylC₁₋₆alkyl, C₁₋₄alkylsulfanylC₁₋₆alkyl,C₁₋₆alkylsulfonylC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₁₋₆alkyl orC₃₋₈cycloalkyl and R¹⁵ is hydrogen, C₁₋₄alkyl, C₁₋₄alkoxyC₁₋₄alkyl orcyanoC₁₋₄alkyl.

More preferably, R¹⁴ is hydrogen, cyano, C₁₋₆alkyl, C₁₋₆alkoxy,C₂₋₆alkenyl, C₂₋₆alkynyl, cyanoC₁₋₆alkyl, C₁₋₆ haloalkyl,C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₆alkoxycarbonylC₁₋₆alkyl, or C₃₋₈cycloalkyl,C₃₋₈cycloalkylC₁₋₆alkyl, phenyl or heteroarylC₁₋₆alkyl, wherein theheteroaryl moiety is a 5-membered monocyclic aromatic ring whichcomprises 1, 2, 3 or 4 heteroatoms individually selected from N, O andS, wherein any of C₃₋₈cycloalkyl, phenyl or heteroaryl, are optionallysubstituted by 1 or 2 substituents selected from R¹⁶, wherein R¹⁶ iscyano, halogen, hydroxy, C₁₋₄alkyl, C₁₋₄ haloalkyl, C₁₋₄alkoxy, C₁₋₄haloalkoxy or C₁₋₄alkoxycarbonyl. Even more preferably, R¹⁴ is hydrogen,C₁₋₆alkyl, C₁₋₆alkoxy, C₂₋₄alkenyl, C₂₋₄alkynyl, C₁₋₂ haloalkyl,C₃₋₆cycloalkyl. Still more preferably, R¹⁴ is hydrogen, methyl, ethyl,propyl, iso-propyl, sec-butyl, methoxy, ethoxy, allyl, propyn-2-yl,2,2,2-trifluoromethyl, cyclopropyl or cyclobutyl.

Preferably, R¹⁵ is hydrogen, methyl, ethyl, C₃₋₄alkynyl or methoxyethyl.More preferably, R¹⁵ is hydrogen, methyl or ethyl, in particular,hydrogen.

In other embodiments, R¹⁵ may be hydrogen, C₁₋₄alkyl,C₁₋₄alkoxyC₁₋₄alkyl or cyanoC₁₋₄alkyl.

R¹⁴ and R¹⁵, together with the nitrogen atom to which they are bonded,may form a 5- or 6-membered cycle optionally containing an additionalheteroatom which is oxygen.

In some embodiments, for the compounds of Formula (I), preferably n is1;

-   -   A¹ to A⁴ are C—H, A¹ is C—F and A² to A⁴ are C—H, A¹ and A² are        C—F and A³ and A⁴ are C—H, A¹ and A³ are C—F and A² and A⁴ are        C—H or A¹ is N and A² to A⁴ are C—H;    -   R⁵ and R⁶ are independently selected from hydrogen, C₁₋₄alkyl        and cyano;    -   R⁷ is hydroxy, C₁₋₄alkyl, C₂₋₄fluoroalkyl, C₁₋₄alkoxy,        hydroxyC₁₋₄alkyl, C₁₋₂alkoxyC₁₋₄alkyl, C₃₋₄alkenyl, C₃₋₄alkynyl,        C₃₋₆ haloalkenyloxy, cyclopropyl, (cyclopropyl)methyl,        phenylC₁₋₂alkoxy, (tetrahydrofuran-2-yl)methyl or        (2-furyl)methyl, wherein any of said cyclopropyl, phenyl,        tetrahydrofuran-2-yl and 2-furyl moieties are optionally        substituted by 1 or 2 substituents selected from cyano, fluoro,        chloro, bromo, methyl, difluoromethyl, trifluoromethyl, methoxy,        ethoxy, or difluoromethoxy;    -   R⁸ is C₁₋₆alkyl, C₁₋₂ haloalkyl, hydroxyC₁₋₆alkyl,        C₁₋₂alkoxyC₁₋₄alkyl, C₃₋₆cycloalkyl or heterocyclyl, wherein the        heterocyclyl moiety is a 4- or 5-membered non-aromatic ring        which comprises 1 or 2 heteroatoms individually selected from N        and O, wherein C₃₋₆cycloalkyl and heterocyclyl are optionally        substituted by 1, 2 or 3 substituents, which may be the same or        different, selected from R⁹; and    -   R⁹ is cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl,        C₂₋₄alkynyl, C₁₋₄ haloalkyl or C₁₋₄alkoxy.

More preferably in the compounds of Formula (I), n is 1;

-   -   A¹ to A⁴ are C—H;    -   R⁵ and R⁶ are independently selected from hydrogen and        C₁₋₄alkyl;    -   R⁷ is C₁₋₄alkyl, C₂₋₄fluoroalkyl, methoxy, ethoxy or        cyclopropyl;    -   R⁸ is C₁₋₆alkyl, C₁₋₂ haloalkyl, hydroxyC₁₋₆alkyl,        C₁₋₂alkoxyC₁₋₄alkyl, C₃₋₆cycloalkyl or heterocyclyl, wherein the        heterocyclyl moiety is a 4- or 5-membered non-aromatic ring        which comprises 1 or 2 heteroatoms individually selected from N        and O, wherein C₃₋₆cycloalkyl and heterocyclyl are optionally        substituted by 1, 2 or 3 substituents, which may be the same or        different, selected from R⁹; and    -   R⁹ is cyano, halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl,        C₂₋₄alkynyl, C₁₋₄ haloalkyl or C₁₋₄alkoxy.

Even more preferably in the compounds of Formula (I), n is 1;

-   -   A¹ to A⁴ are C—H;    -   R⁵ and R⁶ are independently selected from hydrogen and methyl,        preferably hydrogen;    -   R⁷ is methyl, ethyl, n-propyl, iso-propyl, 2,2,2-fluoroethyl,        methoxy, ethoxy or cyclopropyl;    -   R⁸ is C₁₋₄alkyl, C₁₋₂ haloalkyl, hydroxyC₁₋₄alkyl,        C₁₋₂alkoxyC₁₋₂alkyl, C₃₋₆cycloalkyl or heterocyclyl, wherein the        heterocyclyl moiety is a 4- or 5-membered non-aromatic ring        which comprises 1 or 2 heteroatoms which are oxygen, wherein        C₃₋₆cycloalkyl and heterocyclyl are optionally substituted by 1        or 2 substituents, which may be the same or different, selected        from R⁹; and R⁹ is fluoro, chloro, methyl.

In other embodiments, for the compounds of Formula (I), preferably n is1;

-   -   A¹ to A⁴ are C—H;    -   R⁵ and R⁶ are independently selected from hydrogen and methyl;    -   R⁷ is hydroxy, C₂₋₄haloalkyl, C₃₋₆alkenyl, C₃₋₄alkynyl or        C₁₋₄alkoxycarbonyloxy;    -   R⁸ is —OR¹²; and    -   R¹² is hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl, C₃₋₆alkynyl,        C₁₋₄alkoxyC₁₋₆alkyl, phenyl, phenylC₁₋₆alkyl.

More preferably in the compounds of Formula (I), n is 1;

-   -   A¹ to A⁴ are C—H;    -   R⁵ and R⁶ are hydrogen;    -   R⁷ is methoxy;    -   R⁸ is —OR¹²; and    -   R¹² is hydrogen, C₁₋₆alkyl, C₃₋₆alkenyl, C₃₋₆alkynyl, C₁₋₆        haloalkyl, C₁₋₄alkoxyC₁₋₆alkyl, phenyl, phenylC₁₋₆alkyl.

In still other embodiments, for the compounds of Formula (I), preferablyn is 1;

-   -   A¹ to A⁴ are C—H or A¹, A² and A⁴ are C—H and A³ is C—F;    -   R⁵ and R⁶ are hydrogen;    -   R⁷ is hydroxy, C₁₋₄alkyl, C₂₋₄ haloalkyl, C₁₋₄alkoxy,        C₃₋₆alkenyl, C₃₋₄alkynyl, C₃₋₆cycloalkyl;    -   R⁸ is —NR¹⁴R¹⁵;    -   R¹⁴ is hydrogen, cyano, C₁₋₆alkyl, C₁₋₆alkoxy, C₂₋₆alkenyl,        C₂₋₆alkynyl, cyanoC₁₋₆alkyl, C₁₋₆haloalkyl, C₁₋₄alkoxyC₁₋₆alkyl,        C₁₋₆alkoxycarbonylC₁₋₆alkyl, or C₃₋₈cycloalkyl,        C₃₋₈cycloalkylC₁₋₆alkyl, phenyl or heteroarylC₁₋₆alkyl, wherein        the heteroaryl moiety is a 5-membered monocyclic aromatic ring        which comprises 1, 2, 3 or 4 heteroatoms individually selected        from N, O and S, wherein any of C₃₋₈cycloalkyl, phenyl or        heteroaryl, are optionally substituted by 1 or 2 substituents        selected from R¹⁶, wherein R¹⁶ is cyano, halogen, hydroxy,        C₁₋₄alkoxy, C₁₋₄ haloalkoxy or C₁₋₄alkoxycarbonyl; and    -   R¹⁵ is hydrogen, methyl, ethyl, C₃₋₄alkynyl or methoxyethyl.

More preferably in the compounds of Formula (I), n is 1;

-   -   A¹ to A⁴ are C—H;    -   R⁵ and R⁶ are hydrogen;    -   R⁷ is hydroxy, C₁₋₄alkyl, C₂₋₄ haloalkyl, C₁₋₂alkoxy,        C₃₋₄alkenyl, C₃₋₄alkynyl or cyclopropyl;    -   R⁸ is —NR¹⁴R¹⁵;    -   R¹⁴ is hydrogen, methyl, ethyl, propyl, iso-propyl, sec-butyl,        methoxy, ethoxy, allyl, propyn-2-yl, 2,2,2-trifluoromethyl,        cyclopropyl or cyclobutyl; and    -   R¹⁵ is hydrogen, methyl or ethyl.

Even more preferably in the compounds of Formula (I), n is 1;

-   -   A¹ to A⁴ are C—H;    -   R⁵ and R⁶ are hydrogen;    -   R⁷ is C₁₋₄alkyl or C₁₋₂alkoxy;    -   R⁸ is —NR¹⁴R¹⁵;    -   R¹⁴ is hydrogen, methyl, ethyl, propyl, iso-propyl, sec-butyl,        methoxy, ethoxy, allyl, propyn-2-yl, 2,2,2-trifluoromethyl,        cyclopropyl or cyclobutyl; and    -   R¹⁵ is hydrogen.

The compound according to Formula (I) may be selected from compound 1.1to 1.811 listed in Table T1 below, from compound 2.1 to 2.26 listed inTable T2 below, and from compound 3.1 to 3.140 listed in Table T3 below.

The compound of Formula (I) may be a compound according to Formula (IA):

wherein

R¹ and R² are independently selected from hydrogen, chloro, fluoro,methyl, methoxy and trifluoromethyl; and

R³ and R⁴ are independently selected from hydrogen and halogen;

wherein at least two of R¹, R², R³ and R⁴ are hydrogen;

R⁵ and R⁶ are independently selected from hydrogen and C₁₋₄alkyl;

R⁷ is C₁₋₄alkyl or C₁₋₄alkoxy; and

R⁸ hydrogen, C₁₋₆alkyl, C₂₋₆alkenyl, C₂₋₆alkynyl, cyanoC₁₋₆alkyl,C₁₋₆haloalkyl, C₂₋₆haloalkenyl, hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl,C₁₋₄ haloalkoxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl,C₂₋₄alkynyloxyC₁₋₆alkyl, aminoC₁₋₆alkyl, N—C₁₋₄alkylaminoC₁₋₆alkyl,N,N-diC₁₋₄alkylaminoC₁₋₆alkyl, C₁₋₆alkylcarbonylC₁₋₆alkyl,C₁₋₆alkylcarbonylC₂₋₆alkenyl, C₁₋₆alkoxycarbonylC₁₋₆alkyl,C₁₋₆alkylcarbonyloxyC₁₋₆alkyl, N—C₁₋₄alkylaminocarbonylC₁₋₆alkyl,N,N-diC₁₋₄alkylaminocarbonylC₁₋₆alkyl, C₁₋₆alkylsulfanylC₁₋₆alkyl,C₁₋₆alkylsulfonylC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₂₋₆alkynyl, C₂₋₆alkynyloxycarbonylaminoC₁₋₆alkyl; or

R⁸ is C₃₋₈cycloalkylC₀₋₆alkyl, wherein the cycloalkyl moiety isoptionally partially unsaturated, phenylC₀₋₆alkyl, phenylC₂₋₆alkenyl,naphthylC₀₋₆alkyl, heteroarylC₀₋₆alkyl wherein the heteroaryl moiety isa 5- or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, heterodiarylC₀₋₆alkylwherein the heterodiaryl moiety is a 9- or 10-membered bicyclic aromaticsystem which comprises 1, 2, 3 or 4 heteroatoms individually selectedfrom N, O and S, heterocyclylC₀₋₆alkyl wherein the heterocyclyl moietyis a 4- to 6-membered non-aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S, orC₃₋₆cycloalkylcarbonylaminoC₁₋₆alkyl,

wherein for R⁸, any of C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl,phenylC₂₋₆alkenyl, naphthylC₀₋₆alkyl, heteroarylC₀₋₆alkyl,heterodiarylC₀₋₆alkyl, heterocyclylC₀₋₆alkyl andC₃₋₆cycloalkylcarbonylaminoC₁₋₆alkyl moieties are optionally substitutedby 1, 2 or 3 substituents, which may be the same or different, selectedfrom R⁹; wherein

R⁹ is cyano, halogen, hydroxy, C₂₋₄alkenyl, C₂₋₄alkynyl, C₁₋₄ haloalkyl,C₂₋₄ haloalkenyl, C₁₋₄alkoxy, C₁₋₄ haloalkoxy, C₃₋₄alkynyloxy,C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl, carbonylamino,N—C₁₋₄alkylaminocarbonyl, N,N-diC₁₋₄alkylaminocarbonyl orC₁₋₄alkoxycarbonylamino, and wherein R₈ is substitutedC₃₋₈cycloalkylC₀₋₆alkyl or heterocyclylC₀₋₆alkyl, R⁹ may also representoxo on the C₃₋₈cycloalkyl or heterocyclyl moiety; or

wherein for R⁸, any of C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl,phenylC₂₋₆alkenyl, naphthylC₀₋₆alkyl, heteroarylC₀₋₆alkyl,heterodiarylC₀₋₆alkyl, heterocyclylC₀₋₆alkyl andC₃₋₆cycloalkylcarbonylaminoC₁₋₆alkyl moieties are optionally substitutedby 1 substituent selected from R¹⁰; wherein

R¹⁰ is C₃₋₈cycloalkylC₀₋₂alkyl, phenylC₀₋₂alkyl, heteroarylC₀₋₂alkylwherein the heteroaryl moiety is a 5- or 6-membered monocyclic aromaticring which comprises 1, 2, 3 or 4 heteroatoms individually selected fromN, O and S, heterocyclylC₀₋₆alkyl wherein the heterocyclyl moiety is a4- to 6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein any of saidcycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R¹¹; wherein

R¹¹ is hydrogen, cyano, fluoro, chloro, bromo, methyl, trifluoromethyl,methoxy and ethoxy; or

a salt or an N-oxide thereof.

For the compounds of Formula (IA), when R⁸ as a C₃₋₈cycloalkylC₀₋₆alkyl,phenylC₀₋₆alkyl, phenylC₂₋₆alkenyl, naphthylC₀₋₆alkyl,heteroarylC₀₋₆alkyl, heterodiarylC₀₋₆alkyl, heterocyclylC₀₋₆alkyl orC₃₋₆cycloalkylcarbonylaminoC₁₋₆alkyl moiety is indicated as optionallysubstituted by R⁹ or R¹⁰, the cycloalkyl, phenyl, naphthyl, heteroaryl,heterodiaryl, heterocyclyl fragment only may be substituted.

In the compounds of Formula (IA), preferably R¹ and R² are independentlyselected from hydrogen and fluoro. More preferably, R¹ and R² arehydrogen.

In the compounds of Formula (IA), preferably R³ and R⁴ are independentlyselected from hydrogen and fluoro. More preferably, Wand R⁴ arehydrogen.

In the compounds of Formula (IA), preferably three of R¹, R², R³ and R⁴are hydrogen, wherein more preferably R², R³ and R⁴ are hydrogen.

In the compounds of Formula (IA), preferably R⁵ and R⁶ are hydrogen, orR⁵ is hydrogen and R⁶ is C₁₋₄alkyl, preferably methyl or ethyl. Morepreferably, R⁵ and R⁶ are hydrogen.

In the compounds of Formula (IA), preferably R⁷ is methyl, ethyl,propyl, isopropyl, butyl, sec-butyl, methoxy, ethoxy, propoxy,isopropoxy, butoxy, or sec-butoxy. More preferably, R⁷ is methyl, ethyl,sec-butyl, methoxy, ethoxy, or propoxy. Most preferably, R⁷ issec-butyl, methoxy or propoxy.

In the compounds of Formula (IA), preferably R⁸ is hydrogen, C₁₋₆alkyl,C₂₋₆alkenyl, C₂₋₆alkynyl, cyanoC₁₋₆alkyl, C₁₋₆ haloalkyl, C₂₋₆haloalkenyl, hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₄haloalkoxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl,C₂₋₄alkynyloxyC₁₋₆alkyl, C₁₋₆alkylcarbonylC₂₋₆alkenyl,C₁₋₆alkylcarbonyloxyC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₂₋₆alkynyl,C₂₋₆alkynyloxycarbonylaminoC₁₋₆alkyl; or C₃₋₈cycloalkylC₀₋₂alkyl,wherein the cycloalkyl moiety is optionally partially unsaturated,phenylC₀₋₂alkyl, heteroarylC₀₋₂alkyl wherein the heteroaryl moiety is a5- or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, orheterocyclylC₀₋₂alkyl wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S; wherein any of saidC₃₋₈cycloalkylC₀₋₂alkyl, phenylC₀₋₂alkyl, heteroarylC₀₋₂alkyl andheterocyclylC₀₋₂alkyl moieties are optionally substituted by 1, 2 or 3substituents, which may be the same or different, selected from R⁹; andR⁹ is cyano, halogen, hydroxy, C₁₋₄alkyl, C₁₋₄ haloalkyl, C₁₋₄alkoxy,C₂₋₄ haloalkenyl, C₃₋₄alkynyloxy, C₁₋₄alkylcarbonyl andC₁₋₄alkoxycarbonyl.

More preferably, R⁸ is C₁₋₆alkyl, C₂₋₆alkenyl, C₂₋₆alkynyl,C₁₋₆fluoroalkyl, C₁₋₆chloroalkyl, C₁₋₄alkoxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl, C₁₋₆alkylcarbonylC₂₋₆alkenyl,C₁₋₆alkylcarbonyloxyC₁₋₆alkyl, C₁₋₆ alkylsulfonylaminoC₂₋₆alkynyl orC₂₋₆alkynyloxycarbonylaminoC₁₋₆alkyl; C₃₋₈cycloalkylC₀₋₆alkyl,phenylC₀₋₆alkyl, or heterocyclylC₀₋₆alkyl, wherein any of saidcycloalkyl, phenyl, and heterocyclyl moieties are optionally substitutedby 1, 2 or 3 substituents which may be the same or different, selectedfrom R⁹, wherein R⁹ is cyano, halogen, hydroxy, C₁₋₄alkyl, C₁₋₄haloalkyl, C₂₋₄ haloalkenyl, C₃₋₄alkynyloxy, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl; or wherein any of said cycloalkyl, phenyl, andheterocyclyl moieties are optionally substituted by 1 substituentselected from R¹⁰ which is a phenyl.

Even more preferably, R⁸ is C₁₋₆alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl,C₁₋₆fluoroalkyl, C₁₋₄chloroalkyl, C₁₋₄alkoxyC₁₋₄alkyl,C₁₋₄alkoxyC₁₋₂alkoxyC₁₋₄alkyl, C₁₋₄alkylcarbonylC₂₋₄alkenyl,C₁₋₂alkylcarbonyloxyC₁₋₄alkyl, C₁₋₄alkylsulfonylaminoC₂₋₄alkynyl orC₂₋₄alkynyloxycarbonylaminoC₁₋₄alkyl; C₃₋₆cycloalkylC₀₋₁alkyl,phenylC₀₋₁alkyl or heterocyclylC₀₋₁alkyl, wherein any of saidcycloalkyl, phenyl, and heterocyclyl moieties are optionally substitutedby 1, 2 or 3 substituents which may be the same or different, selectedfrom R⁹, wherein R⁹ is cyano, fluoro, chloro, hydroxy, methyl, ethyl,trifluoromethyl, 2,2-dichloroethenyl, propynyloxy, acetyl,methoxycarbonyl; or wherein any of said cycloalkyl, phenyl, andheterocyclyl moieties are optionally substituted by 1 substituentselected from R¹⁰ which is a phenyl.

In some embodiments of the invention according to Formula (IA) where R⁸is a group selected from C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl,phenylC₂₋₆alkenyl, naphthylC₀₋₆alkyl, heteroarylC₀₋₆alkyl,heterodiarylC₀₋₆alkyl, heterocyclylC₀₋₆alkyl, preferably R⁸ isC₃₋₈cycloalkylC₀₋₂alkyl, phenylC₀₋₂alkyl, phenylC₂₋₄alkenyl,naphthylC₀₋₂alkyl, heteroarylC₀₋₂alkyl, heterodiarylC₀₋₂alkyl orheterocyclylC₀₋₂alkyl.

In some embodiments of the invention according to Formula (IA) where R⁸is a group selected from C₃₋₈cycloalkylC₀₋₆alkyl, preferablyC₃₋₈cycloalkyl is cyclopropyl, cyclobutyl, cyclopentyl or cyclohexyl.

In some embodiments of the invention according to Formula (IA) where R⁸is a group selected from phenylC₀₋₆alkyl, preferably, R⁸ is phenyl orbenzyl.

In some embodiments of the invention according to Formula (IA) where R⁸is a group selected from heterocyclylC₀₋₆alkyl, preferably theheterocyclyl group has 1 or 2 heteroatoms selected from N, O and S. Morepreferably, the heterocyclyl group has a single heteroatom selected fromO and S. Most preferable for R⁸ as a heterocyclylC₀₋₆alkyl are oxetanyl,tetrahydrofuranyl, tetrahydropyranyl, thietanyl ortetrahydrothiopyranyl.

-   -   In the compounds of Formula (IA), preferably R¹ and R² are        independently selected from hydrogen and fluoro;    -   R³ and R⁴ are independently selected from hydrogen and fluoro;    -   wherein at least two of R¹, R², R³ and R⁴ are hydrogen,    -   R⁵ and R⁶ are hydrogen, or R⁵ is hydrogen and R⁶ is methyl;    -   R⁷ is C₁₋₄alkyl or C₁₋₄alkoxy; and    -   R⁸ is C₁₋₆alkyl, C₂₋₆alkenyl, C₂₋₆alkynyl, C₁₋₆fluoroalkyl,        C₁₋₆chloroalkyl, C₁₋₄alkoxyC₁₋₆alkyl,        C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl, C₁₋₆alkylcarbonylC₂₋₆alkenyl,        C₁₋₆alkylcarbonyloxyC₁₋₆alkyl, C₁₋₆        alkylsulfonylaminoC₂₋₆alkynyl or        C₂₋₆alkynyloxycarbonylaminoC₁₋₆alkyl; C₃₋₈cycloalkylC₀₋₆alkyl,        phenylC₀₋₆alkyl, or heterocyclylC₀₋₆alkyl, wherein any of said        cycloalkyl, phenyl, and heterocyclyl moieties are optionally        substituted by 1, 2 or 3 substituents which may be the same or        different, selected from R⁹, wherein R⁹ is cyano, halogen,        hydroxy, C₁₋₄alkyl, C₁₋₄haloalkyl, C₂₋₄ haloalkenyl,        C₃₋₄alkynyloxy, C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl; or        wherein any of said cycloalkyl, phenyl, and heterocyclyl        moieties are optionally substituted by 1 substituent selected        from R¹⁰ which is a phenyl.    -   In the compounds of Formula (IA), more preferably R¹ and R² are        independently selected from hydrogen and fluoro;    -   R³ and R⁴ are independently selected from hydrogen and fluoro;    -   wherein at least two of R¹, R², R³ and R⁴ are hydrogen    -   R⁵ and R⁶ are hydrogen, or R⁵ is hydrogen and R⁶ is methyl;    -   R⁷ is methoxy, propoxy or sec-butyl; and    -   R⁸ is C₁₋₆alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl, C₁₋₆fluoroalkyl,        C₁₋₄chloroalkyl, C₁₋₄alkoxyC₁₋₄alkyl,        C₁₋₄alkoxyC₁₋₂alkoxyC₁₋₄alkyl, C₁₋₄alkylcarbonylC₂₋₄alkenyl,        C₁₋₂alkylcarbonyloxyC₁₋₄alkyl, C₁₋₄alkylsulfonylaminoC₂₋₄alkynyl        or C₂₋₄alkynyloxycarbonylaminoC₁₋₄alkyl; C₃₋₆cycloalkylC₀₋₁        alkyl, phenylC₀₋₁alkyl or heterocyclylC₀₋₁alkyl, wherein any of        said cycloalkyl, phenyl, and heterocyclyl moieties are        optionally substituted by 1, 2 or 3 substituents which may be        the same or different, selected from R⁹, wherein R⁹ is cyano,        fluoro, chloro, hydroxy, methyl, ethyl, trifluoromethyl,        2,2-dichloroethenyl, propynyloxy, acetyl, methoxycarbonyl; or        wherein any of said cycloalkyl, phenyl, and heterocyclyl        moieties are optionally substituted by 1 substituent selected        from R¹⁰ which is a phenyl.    -   In the compounds of Formula (IA), even more preferably, R¹ and        R² are hydrogen;    -   R³ and R⁴ are hydrogen;    -   R⁵ and R⁶ are hydrogen;    -   R⁷ is methoxy, propoxy or sec-butyl; and    -   R⁸ is C₁₋₆alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl, C₁₋₆fluoroalkyl,        C₁₋₄chloroalkyl, C₁₋₄alkoxyC₁₋₄alkyl,        C₁₋₄alkoxyC₁₋₂alkoxyC₁₋₄alkyl, C₁₋₄alkylcarbonylC₂₋₄alkenyl,        C₁₋₂alkylcarbonyloxyC₁₋₄alkyl, C₁₋₄alkylsulfonylaminoC₂₋₄alkynyl        or C₂₋₄alkynyloxycarbonylaminoC₁₋₄alkyl;        C₃₋₆cycloalkylC₀₋₁alkyl, phenylC₀₋₁alkyl or        heterocyclylC₀₋₁alkyl, wherein any of said cycloalkyl, phenyl,        and heterocyclyl moieties are optionally substituted by 1, 2 or        3 substituents which may be the same or different, selected from        R⁹, wherein R⁹ is cyano, fluoro, chloro, hydroxy, methyl, ethyl,        trifluoromethyl, 2,2-dichloroethenyl, propynyloxy, acetyl,        methoxycarbonyl; or wherein any of said cycloalkyl, phenyl, and        heterocyclyl moieties are optionally substituted by 1        substituent selected from R¹⁰ which is a phenyl.

The compounds of the present invention may be enantiomers of thecompound of Formula (I) as represented by a Formula (Ia) or a Formula(Ib) when n is 1, wherein R⁵ and R⁶ are different (see below), or indeedwhen n is 2 and at only one of the two carbon positions bound to R⁵ andR⁶, R⁵ and R⁶ are different.

Likewise, the compounds of the present invention may be diastereomers ofthe compound of Formula (I) when n is 2, and wherein at each of the twocarbon positions bound to R⁵ and R⁶, R⁵ and R⁶ are different.

It is understood that when in aqueous media, the compounds of formula(I) according to the invention may be present in a reversibleequilibrium with the corresponding covalently hydrated forms (ie, thecompounds of formula (I-I) and formula (I-II) as shown below) at theCF₃-oxadiazole motif. This dynamic equilibrium may be important for thebiological activity of the compounds of Formula (I). The designations ofn, A¹, A², A³, A⁴, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹, R¹⁰, R¹¹, R¹²,R¹³, R¹⁴, R¹⁵, R¹⁶ and R¹⁷ with reference to the compounds of formula(I) of the present invention apply generally to the compounds of Formula(I-I) and Formula (I-II), as well as to the specific disclosures ofcombinations of n, A¹, A², A³, A⁴, R¹, R², R³, R⁴, R⁵, R⁶, R⁷, R⁸, R⁹,R¹⁰, R¹¹, R¹², R¹³, R¹⁴, R¹⁵, R¹⁶ and R¹⁷ as represented in Tables 1.1to 1.29, 2.1 to 2.5, 3.1 to 3.14 and 4.1 to 4.4 below or the compounds1.1 to 1.811 described in Table T1 (below), the compounds 2.1 to 2.26described in Table T2 (below), and the compounds 3.1 to 3.140 describedin Table T3 (below).

Compounds of the present invention can be made as shown in the followingschemes 1 to 14, in which, unless otherwise stated, the definition ofeach variable is as defined above for a compound of formula (I).

The compounds of formula (I) can be obtained by an amide couplingtransformation with compounds of formula (II) and compounds of formula(III) by activating the carboxylic acid function of the compounds offormula (III), a process that usually takes place by converting the —OHof the carboxylic acid into a good leaving group, such as a chloridegroup, for example by using (COCl)₂ or SOCl₂, prior to treatment withthe compounds of formula (II), preferably in a suitable solvent (eg,dimethylformamide, dichloromethane or tetrahydrofuran), preferably at atemperature of between 25° C. and 100° C., and optionally in thepresence of a base such as triethylamine or N,N-diisopropylethylamine,or under conditions described in the literature for an amide coupling.For examples, see WO 2003/028729. Compounds of formula (III) arecommercially available or prepared using known methods. For relatedexamples, see: Nelson, T. D et al Tetrahedron Lett. (2004), 45, 8917;Senthil, K. et al Pest. Res. Journal (2009), 21, 133; and Crich, D.,Zou, Y. J. Org. Chem. (2005), 70, 3309. This reaction is shown in Scheme1.

Alternatively, compounds of formula (I) can be prepared from compoundsof formula (II) via treatment with triphosgene, in a suitable solvent(eg, ethyl acetate, CHCl₃, or toluene) with heating between 65° C. and100° C. followed by the addition of suitable nucleophiles of formula(IV), wherein R⁸—Nu is an organometallic (eg, an organomagnesium,organozinc, or organolithium) reagent in a suitable solvent (eg,toluene, diethyl ether or tetrahydrofuran) at a temperature between −78°C. and 25° C. For related examples, see Charalambides, Y. C., Moratti,S. C. Synth. Commun. (2007), 37, 1037; Schaefer, G. et al Angew. Chem.,Int. Ed. (2012) 51, 9173; Lengyel, I. et al Heterocycles (2007), 73,349; and Benalil, A et al Synthesis (1991), 9, 787. Furthermore,compounds of formula (I) can be prepared from compounds of formula (II)via treatment with triphosgene, in a suitable solvent (eg,1,2-dichloroethane, CHCl₃, or toluene) followed by the addition ofsuitable nucleophiles of formula (IV), wherein R⁸—Nu represents HOR¹⁰ orHN(R¹¹)R¹² in the presence of a suitable base such as triethylamine.This reaction is shown in Scheme 2

Additionally, compounds of formula (I) can be prepared from compounds offormula (V) by treatment with trifluoroacetic anhydride in the presenceof a base (eg, pyridine or 4-dimethylaminopyridine) in a suitablesolvent, such as tetrahydrofuran or ethanol, at a temperature between25° C. and 75° C. For related examples, see WO 2003/028729 and WO2010/045251. This reaction is shown in Scheme 3.

Compounds of formula (V) can be prepared from compounds of formula (VI)by treatment with a hydroxylamine hydrochloride salt in the presence ofa base, such as triethylamine, in a suitable solvent, such as methanol,at a temperature between 0° C. and 100° C. For related examples, seeKitamura, S. et al Chem. Pharm. Bull. (2001), 49, 268 and WO2013/066838. This reaction is shown in Scheme 4.

Compounds of formula (VI) can be prepared from compounds of formula(VII), wherein Z is Br or I, via metal-promoted reaction with a suitablecyanide reagent, such as Pd(0)/Zn(CN)₂ or CuCN, in a suitable solvent(eg, dimethylformamide or N-methylpyrrolidone) at elevated temperaturebetween 100° C. and 120° C. For related examples, see US 2007/0155739and WO 2009/022746. This reaction is shown in Scheme 5.

Compounds of formula (VII), wherein the N—R⁷ bond contains a directlylinked —CH₂ segment, can be prepared from compounds of formula (VIII),wherein Z is Br or I, via a base-promoted reaction (eg, sodium hydride)with a suitable alkylating reagent (eg, methyl iodide or propyl iodide),in a suitable solvent (eg, dimethylformamide or N-methylpyrrolidone) atelevated temperature between 100° C. and 120° C. This reaction is shownin Scheme 6.

Compounds of formula (II), wherein n is preferably 0 and R⁶ is hydrogen,can be prepared from carbonyl compounds of formula (IX), starting withtreatment by compounds of formula (X), wherein R^(PG) istert-butylsulfinamide, optionally in the presence of an activatingreagent (eg, Ti(OEt)₄), in a suitable solvent, (eg, tetrahydrofuran) ata temperature between 60° C. and 75° C. and followed by the addition ofa reagent of formula (XI), such as an alkyl Grignard reagent (eg.alkylMgBr), Me₃SiCN, or a metal hydride (eg, NaBH₄, NaBH₃CN, or LiAlH₄),in a suitable solvent, (eg, tetrahydrofuran or ethanol) at temperaturesbetween 0° C. and 25° C. Removal of the tert-butanesulfinyl group withconcomitant liberation of amine compounds of formula (II) occurs upontreatment with methanolic HCl. For related examples, see Cogan, D.,Ellman J. A. J. Am. Chem. Soc. (1999), 121, 268. This reaction is shownin Scheme 7.

Alternatively, compounds of formula (II), wherein n is preferably 1, canbe prepared from compounds of formula (XIII), wherein X is Cl or Br, bytreatment with amines of formula (XII), wherein Y istert-butylcarboxylate, in a suitable solvent (eg, tetrahydrofuran) at atemperature between 25° C. and 60° C. Removal of thetert-butylcarboxylate groups with concomitant liberation of benzylaminesof formula (II) occurs upon treatment with HCl or trifluoroacetic acidin a suitable solvent (eg, dioxane or MeOH). For related examples, seeMiyawaki, K. et al Heterocycles (2001), 54, 887, WO 2003/028729, and WO2013/066839. This reaction is shown in Scheme 8.

Compounds of formula (XIII), wherein n is 1, can be prepared fromcompounds of formula (XIV), wherein X is Cl or Br, by treatment with ahalogen source (eg, N-bromosuccinimide (NBS) or N-chlorosuccinimide(NCS)) and a radical initiator (eg, (PhCO₂)₂ or azobisisobutyronitrile(AIBN)) in a suitable solvent, such as tetrachloromethane, attemperatures between 55° and 100° C. in the presence of ultravioletlight. For related examples, see Liu, S. et al Synthesis (2001), 14,2078 and Kompella, A. et al Org. Proc. Res. Dev. (2012), 16, 1794. Thisreaction is shown in Scheme 9.

The compounds of formula (VII) can be obtained by an amide couplingtransformation with compounds of formula (XV) and compounds of formula(III) by activating the carboxylic acid function of the compounds offormula (III), a process that usually takes place by converting the —OHof the carboxylic acid into a good leaving group, such as a chloridegroup, for example by using (COCl)₂ or SOCl₂, prior to treatment withthe compounds of formula (XV), preferably in a suitable solvent (eg,dimethylformamide, dichloromethane or tetrahydrofuran), preferably at atemperature of between 25° C. and 100° C., and optionally in thepresence of a base such as triethylamine or N,N-diisopropylethylamine,or under conditions described in the literature for an amide coupling.For examples, see WO 2003/028729. Compounds of formula (III) arecommercially available or prepared using known methods. For relatedexamples, see: Nelson, T. D et al Tetrahedron Lett. (2004), 45, 8917;Senthil, K. et al Pest. Res. Journal (2009), 21, 133; and Crich, D.,Zou, Y. J. Org. Chem. (2005), 70, 3309. This reaction is shown in Scheme10.

Furthermore, compounds of formula (VII), wherein Z is Br, I, or CN andR⁸ may also be OR¹² or NR¹⁴R¹⁵ where R¹⁵ is not hydrogen and n ispreferably 1, can be prepared from compounds of formula (XVIII), whereinX is Cl, Br or I, via treatment with amides of formula (XVII), wherein Yis tert-butylcarboxylate, in the presence of a suitable base, such asNaH, in a suitable solvent, such as dimethylformamide, at a temperaturebetween 0° C. and 100° C. In some cases, a better reaction performancemay be gained from the use of a catalyst (eg, Nal or4-dimethylaminopyridine) and with microwave irradiation. Removal of thetert-butylcarboxylate groups with concomitant liberation of benzylamidesof formula (VIII) occurs upon treatment with HCl or trifluoroacetic acidin a suitable solvent (eg, dioxane, dichloromethane or MeOH). Forrelated examples, see Miyawaki, K. et al Heterocycles (2001), 54, 887.This reaction is shown in Scheme 11.

Compounds of formula (XVIII), wherein Z is Br, I, or CN and X is Cl orBr and n is preferably 1, are either commercially available or can beprepared from compounds of formula (XIX), by treatment with a halogensource, (eg, N-bromosuccinimide (NBS) or N-chlorosuccinimide (NCS)) anda radical initiator, such as (PhCO₂)₂ or azobisisobutyronitrile (AIBN),in the presence of ultraviolet light, in a suitable solvent, such astetrachloromethane, at temperatures between 55° C. and 100° C. Forrelated examples, see Liu, S. et al Synthesis (2001), 14, 2078 andKompella, A. et al Org. Proc. Res. Dev. (2012), 16, 1794. This reactionis shown in Scheme 12.

Alternatively, compounds of formula (XVIII), wherein X is Cl, Br, I, orOSO₂Me and Z is Br, I and n is preferably 1, or CN are eithercommercially available or can be prepared from compounds of formula(XX), by treatment with a halogen source (eg, CBr₄, CCl₄ or I₂) in thepresence of triphenylphosphine, or with methanesulfonyl chloride(CISO₂Me), in a suitable solvent, (eg, dichloromethane) at a temperaturebetween 0° C. and 100° C. For related examples, see Liu, H. et alBioorg. Med. Chem. (2008), 16, 10013, WO 2014/020350 and Kompella, A. etal Bioorg. Med. Chem. Lett. (2001), 1, 3161. Compounds of formula (XIX)are commercially available. This reaction is shown in Scheme 13.

Compounds of formula (XV), wherein n is 0 or 1, and R⁶ is preferablyhydrogen, can be prepared from compounds of formula (XXI), starting withtreatment by compounds of formula (X), wherein R^(PG) is atert-butylsulfinamides or hydrogen, optionally in the presence of anactivating reagent (eg, Ti(OEt)₄), in a suitable solvent, (eg,tetrahydrofuran) at a temperature between 60° C. and 75° C. and followedby the addition of an organometallic compound of formula (XI), such asan alkyl Grignard reagent (eg. alkylMgBr) and Me₃SiCN, or a metalhydride of formula (XI), wherein the metal is B or Al (eg, NaBH₄,NaBH₃CN, or LiAlH₄), in a suitable solvent, (eg, tetrahydrofuran orethanol) at temperatures between 0° C. and 25° C. Removal of thetert-butanesulfinyl group with concomitant liberation of benzylamines offormula (XV) occurs upon treatment with methanolic HCl. For relatedexamples, see Cogan, D., Ellman J. A. J. Am. Chem. Soc. (1999), 121,268. This reaction is shown in Scheme 14.

As already indicated, surprisingly, it has now been found that the novelcompounds of formula (I) according to the invention have, for practicalpurposes, a very advantageous level of biological activity forprotecting plants against diseases that are caused by fungi.

The compounds of formula (I) can be used in the agricultural sector andrelated fields of use, e.g., as active ingredients for controlling plantpests or on non-living materials for the control of spoilagemicroorganisms or organisms potentially harmful to man. The novelcompounds are distinguished by excellent activity at low rates ofapplication, by being well tolerated by plants and by beingenvironmentally safe. They have very useful curative, preventive andsystemic properties and can be used for protecting numerous cultivatedplants. The compounds of formula I can be used to inhibit or destroy thepests that occur on plants or parts of plants (fruit, blossoms, leaves,stems, tubers, roots) of different crops of useful plants, while at thesame time protecting also those parts of the plants that grow later,e.g., from phytopathogenic microorganisms.

The present invention further relates to a method for controlling orpreventing infestation of plants or plant propagation material and/orharvested food crops susceptible to microbial attack by treating plantsor plant propagation material and/or harvested food crops wherein aneffective amount a compound of formula (I) is applied to the plants, toparts thereof or the locus thereof.

It is also possible to use compounds of formula (I) as fungicide. Theterm “fungicide” as used herein means a compound that controls,modifies, or prevents the growth of fungi. The term “fungicidallyeffective amount” means the quantity of such a compound or combinationof such compounds that is capable of producing an effect on the growthof fungi. Controlling or modifying effects include all deviation fromnatural development, such as killing, retardation and the like, andprevention includes barrier or other defensive formation in or on aplant to prevent fungal infection.

It may also be possible to use compounds of formula (I) as dressingagents for the treatment of plant propagation material, e.g., seed, suchas fruits, tubers or grains, or plant cuttings, for the protectionagainst fungal infections as well as against phytopathogenic fungioccurring in the soil. The propagation material can be treated with acomposition comprising a compound of formula (I) before planting: seed,for example, can be dressed before being sown. The active compounds offormula (I) can also be applied to grains (coating), either byimpregnating the seeds in a liquid formulation or by coating them with asolid formulation. The composition can also be applied to the plantingsite when the propagation material is being planted, for example, to theseed furrow during sowing. The invention relates also to such methods oftreating plant propagation material and to the plant propagationmaterial so treated.

Furthermore, the compounds of formula (I) can be used for controllingfungi in related areas, for example in the protection of technicalmaterials, including wood and wood related technical products, in foodstorage, in hygiene management.

In addition, the invention could be used to protect non-living materialsfrom fungal attack, e.g. lumber, wall boards and paint.

The compounds of formula (I) are for example, effective against fungiand fungal vectors of disease as well as phytopathogenic bacteria andviruses. These fungi and fungal vectors of disease as well asphytopathogenic bacteria and viruses are for example:

Absidia corymbifera, Alternaria spp, Aphanomyces spp, Ascochyta spp,Aspergillus spp. including A. flavus, A. fumigatus, A. nidulans, A.niger, A. terrus, Aureobasidium spp. including A. pullulans, Blastomycesdermatitidis, Blumeria graminis, Bremia lactucae, Botryosphaeria spp.including B. dothidea, B. obtusa, Botrytis spp. inclusing B. cinerea,Candida spp. including C. albicans, C. glabrata, C. krusei, C.lusitaniae, C. parapsilosis, C. tropicalis, Cephaloascus fragrans,Ceratocystis spp, Cercospora spp. including C. arachidicola,Cercosporidium personatum, Cladosporium spp, Claviceps purpurea,Coccidioides immitis, Cochliobolus spp, Colletotrichum spp. including C.musae, Cryptococcus neoformans, Diaporthe spp, Didymella spp, Drechsleraspp, Elsinoe spp, Epidermophyton spp, Erwinia amylovora, Erysiphe spp.including E. cichoracearum, Eutypa lata, Fusarium spp. including F.culmorum, F. graminearum, F. langsethiae, F. moniliforme, F. oxysporum,F. proliferatum, F. subglutinans, F. solani, Gaeumannomyces graminis,Gibberella fujikuroi, Gloeodes pomigena, Gloeosporium musarum,Glomerella cingulate, Guignardia bidwellii, Gymnosporangiumjuniperi-virginianae, Helminthosporium spp, Hemileia spp, Histoplasmaspp. including H. capsulatum, Laetisaria fuciformis, Leptographiumlindbergi, Leveillula taurica, Lophodermium seditiosum, Microdochiumnivale, Microsporum spp, Monilinia spp, Mucor spp, Mycosphaerella spp.including M. graminicola, M. pomi, Oncobasidium theobromaeon, Ophiostomapiceae, Paracoccidioides spp, Penicillium spp. including P. digitatum,P. italicum, Petriellidium spp, Peronosclerospora spp. Including P.maydis, P. philippinensis and P. sorghi, Peronospora spp, Phaeosphaerianodorum, Phakopsora pachyrhizi, Phellinus igniarus, Phialophora spp,Phoma spp, Phomopsis viticola, Phytophthora spp. including P. infestans,Plasmopara spp. including P. halstedii, P. viticola, Pleospora spp.,Podosphaera spp. including P. leucotricha, Polymyxa graminis, Polymyxabetae, Pseudocercosporella herpotrichoides, Pseudomonas spp,Pseudoperonospora spp. including P. cubensis, P. humuli, Pseudopezizatracheiphila, Puccinia Spp. including P. hordei, P. recondita, P.striiformis, P. triticina, Pyrenopeziza spp, Pyrenophora spp,Pyricularia spp. including P. oryzae, Pythium spp. including P. ultimum,Ramularia spp, Rhizoctonia spp, Rhizomucor pusillus, Rhizopus arrhizus,Rhynchosporium spp, Scedosporium spp. including S. apiospermum and S.prolificans, Schizothyrium pomi, Sclerotinia spp, Sclerotium spp,Septoria spp, including S. nodorum, S. tritici, Sphaerotheca macularis,Sphaerotheca fusca (Sphaerotheca fuliginea), Sporothorix spp,Stagonospora nodorum, Stemphylium spp., Stereum hirsutum, Thanatephoruscucumeris, Thielaviopsis basicola, Tilletia spp, Trichoderma spp.including T. harzianum, T. pseudokoningii, T. viride, Trichophyton spp,Typhula spp, Uncinula necator, Urocystis spp, Ustilago spp, Venturiaspp. including V. inaequalis, Verticillium spp, and Xanthomonas spp.

The compounds of formula (I) may be used for example on turf,ornamentals, such as flowers, shrubs, broad-leaved trees or evergreens,for example conifers, as well as for tree injection, pest management andthe like.

Within the scope of present invention, target crops and/or useful plantsto be protected typically comprise perennial and annual crops, such asberry plants for example blackberries, blueberries, cranberries,raspberries and strawberries; cereals for example barley, maize (corn),millet, oats, rice, rye, sorghum triticale and wheat; fibre plants forexample cotton, flax, hemp, jute and sisal; field crops for examplesugar and fodder beet, coffee, hops, mustard, oilseed rape (canola),poppy, sugar cane, sunflower, tea and tobacco; fruit trees for exampleapple, apricot, avocado, banana, cherry, citrus, nectarine, peach, pearand plum; grasses for example Bermuda grass, bluegrass, bentgrass,centipede grass, fescue, ryegrass, St. Augustine grass and Zoysia grass;herbs such as basil, borage, chives, coriander, lavender, lovage, mint,oregano, parsley, rosemary, sage and thyme; legumes for example beans,lentils, peas and soya beans; nuts for example almond, cashew, groundnut, hazelnut, peanut, pecan, pistachio and walnut; palms for exampleoil palm; ornamentals for example flowers, shrubs and trees; othertrees, for example cacao, coconut, olive and rubber; vegetables forexample asparagus, aubergine, broccoli, cabbage, carrot, cucumber,garlic, lettuce, marrow, melon, okra, onion, pepper, potato, pumpkin,rhubarb, spinach and tomato; and vines for example grapes.

The term “useful plants” is to be understood as also including usefulplants that have been rendered tolerant to herbicides like bromoxynil orclasses of herbicides (such as, for example, HPPD inhibitors, ALSinhibitors, for example primisulfuron, prosulfuron and trifloxysulfuron,EPSPS (5-enol-pyrovyl-shikimate-3-phosphate-synthase) inhibitors, GS(glutamine synthetase) inhibitors or PPO (protoporphyrinogen-oxidase)inhibitors) as a result of conventional methods of breeding or geneticengineering. An example of a crop that has been rendered tolerant toimidazolinones, e.g. imazamox, by conventional methods of breeding(mutagenesis) is Clearfield® summer rape (Canola). Examples of cropsthat have been rendered tolerant to herbicides or classes of herbicidesby genetic engineering methods include glyphosate- andglufosinate-resistant maize varieties commercially available under thetrade names RoundupReady®, Herculex I® and LibertyLink®.

The term “useful plants” is to be understood as also including usefulplants which have been so transformed by the use of recombinant DNAtechniques that they are capable of synthesising one or more selectivelyacting toxins, such as are known, for example, from toxin-producingbacteria, especially those of the genus Bacillus.

Examples of such plants are: YieldGard® (maize variety that expresses aCryIA(b) toxin); YieldGard Rootworm® (maize variety that expresses aCryIIIB(b1) toxin); YieldGard Plus® (maize variety that expresses aCryIA(b) and a CryIIIB(b1) toxin); Starlink® (maize variety thatexpresses a Cry9(c) toxin); Herculex I® (maize variety that expresses aCryIF(a2) toxin and the enzyme phosphinothricine N-acetyltransferase(PAT) to achieve tolerance to the herbicide glufosinate ammonium);NuCOTN 33B® (cotton variety that expresses a CryIA(c) toxin); BollgardI® (cotton variety that expresses a CryIA(c) toxin); Bollgard 11®(cotton variety that expresses a CryIA(c) and a CryIIA(b) toxin);VIPCOT® (cotton variety that expresses a VIP toxin); NewLeaf® (potatovariety that expresses a CryIIIA toxin); NatureGard® Agrisure® GTAdvantage (GA21 glyphosate-tolerant trait), Agrisure® CB Advantage (Bt11corn borer (CB) trait), Agrisure® RW (corn rootworm trait) andProtecta®.

The term “crops” is to be understood as including also crop plants whichhave been so transformed by the use of recombinant DNA techniques thatthey are capable of synthesising one or more selectively acting toxins,such as are known, for example, from toxin-producing bacteria,especially those of the genus Bacillus.

Toxins that can be expressed by such transgenic plants include, forexample, insecticidal proteins from Bacillus cereus or Bacilluspopilliae; or insecticidal proteins from Bacillus thuringiensis, such asδ-endotoxins, e.g. Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A,Cry3Bb1 or Cry9C, or vegetative insecticidal proteins (Vip), e.g. Vip1,Vip2, Vip3 or Vip3A; or insecticidal proteins of bacteria colonisingnematodes, for example Photorhabdus spp. or Xenorhabdus spp., such asPhotorhabdus luminescens, Xenorhabdus nematophilus; toxins produced byanimals, such as scorpion toxins, arachnid toxins, wasp toxins and otherinsect-specific neurotoxins; toxins produced by fungi, such asStreptomycetes toxins, plant lectins, such as pea lectins, barleylectins or snowdrop lectins; agglutinins; proteinase inhibitors, such astrypsin inhibitors, serine protease inhibitors, patatin, cystatin,papain inhibitors; ribosome-inactivating proteins (RIP), such as ricin,maize-RIP, abrin, luffin, saporin or bryodin; steroid metabolismenzymes, such as 3-hydroxysteroidoxidase,ecdysteroid-UDP-glycosyl-transferase, cholesterol oxidases, ecdysoneinhibitors, HMG-COA-reductase, ion channel blockers, such as blockers ofsodium or calcium channels, juvenile hormone esterase, diuretic hormonereceptors, stilbene synthase, bibenzyl synthase, chitinases andglucanases.

Further, in the context of the present invention there are to beunderstood by δ-endotoxins, for example Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2,Cry2Ab, Cry3A, Cry3Bb1 or Cry9C, or vegetative insecticidal proteins(Vip), for example Vip1, Vip2, Vip3 or Vip3A, expressly also hybridtoxins, truncated toxins and modified toxins. Hybrid toxins are producedrecombinantly by a new combination of different domains of thoseproteins (see, for example, WO 02/15701). Truncated toxins, for examplea truncated Cry1Ab, are known. In the case of modified toxins, one ormore amino acids of the naturally occurring toxin are replaced. In suchamino acid replacements, preferably non-naturally present proteaserecognition sequences are inserted into the toxin, such as, for example,in the case of Cry3A055, a cathepsin-G-recognition sequence is insertedinto a Cry3A toxin (see WO 03/018810).

Examples of such toxins or transgenic plants capable of synthesisingsuch toxins are disclosed, for example, in EP-A-0 374 753, WO93/07278,WO95/34656, EP-A-0 427 529, EP-A-451 878 and WO 03/052073.

The processes for the preparation of such transgenic plants aregenerally known to the person skilled in the art and are described, forexample, in the publications mentioned above. CryI-type deoxyribonucleicacids and their preparation are known, for example, from WO 95/34656,EP-A-0 367 474, EP-A-0 401 979 and WO 90/13651.

The toxin contained in the transgenic plants imparts to the plantstolerance to harmful insects. Such insects can occur in any taxonomicgroup of insects, but are especially commonly found in the beetles(Coleoptera), two-winged insects (Diptera) and butterflies(Lepidoptera).

Transgenic plants containing one or more genes that code for aninsecticidal resistance and express one or more toxins are known andsome of them are commercially available. Examples of such plants are:YieldGard® (maize variety that expresses a Cry1Ab toxin); YieldGardRootworm® (maize variety that expresses a Cry3Bb1 toxin); YieldGardPlus® (maize variety that expresses a Cry1Ab and a Cry3Bb1 toxin);Starlink® (maize variety that expresses a Cry9C toxin); Herculex I®(maize variety that expresses a Cry1Fa2 toxin and the enzymephosphinothricine N-acetyltransferase (PAT) to achieve tolerance to theherbicide glufosinate ammonium); NuCOTN 33B® (cotton variety thatexpresses a Cry1Ac toxin); Bollgard I® (cotton variety that expresses aCry1Ac toxin); Bollgard II® (cotton variety that expresses a Cry1Ac anda Cry2Ab toxin); VipCot® (cotton variety that expresses a Vip3A and aCry1Ab toxin); NewLeaf® (potato variety that expresses a Cry3A toxin);NatureGard®, Agrisure® GT Advantage (GA21 glyphosate-tolerant trait),Agrisure® CB Advantage (Bt11 corn borer (CB) trait) and Protecta®.

Further examples of such transgenic crops are:

-   1. Bt11 Maize from Syngenta Seeds SAS, Chemin de l′Hobit 27, F-31    790 St. Sauveur, France, registration number C/FR/96/05/10.    Genetically modified Zea mays which has been rendered resistant to    attack by the European corn borer (Ostrinia nubilalis and Sesamia    nonagrioides) by transgenic expression of a truncated Cry1Ab toxin.    Bt11 maize also transgenically expresses the enzyme PAT to achieve    tolerance to the herbicide glufosinate ammonium.-   2. Bt176 Maize from Syngenta Seeds SAS, Chemin de l′Hobit 27, F-31    790 St. Sauveur, France, registration number C/FR/96/05/10.    Genetically modified Zea mays which has been rendered resistant to    attack by the European corn borer (Ostrinia nubilalis and Sesamia    nonagrioides) by transgenic expression of a Cry1Ab toxin. Bt176    maize also transgenically expresses the enzyme PAT to achieve    tolerance to the herbicide glufosinate ammonium.-   3. MIR604 Maize from Syngenta Seeds SAS, Chemin de l′Hobit 27, F-31    790 St. Sauveur, France, registration number C/FR/96/05/10. Maize    which has been rendered insect-resistant by transgenic expression of    a modified Cry3A toxin. This toxin is Cry3A055 modified by insertion    of a cathepsin-G-protease recognition sequence. The preparation of    such transgenic maize plants is described in WO 03/018810.-   4. MON 863 Maize from Monsanto Europe S.A. 270-272 Avenue de    Tervuren, B-1150 Brussels, Belgium, registration number C/DE/02/9.    MON 863 expresses a Cry3Bb1 toxin and has resistance to certain    Coleoptera insects.-   5. IPC 531 Cotton from Monsanto Europe S.A. 270-272 Avenue de    Tervuren, B-1150 Brussels, Belgium, registration number C/ES/96/02.-   6. 1507 Maize from Pioneer Overseas Corporation, Avenue Tedesco, 7    B-1160 Brussels, Belgium, registration number C/NL/00/10.    Genetically modified maize for the expression of the protein Cry1F    for achieving resistance to certain Lepidoptera insects and of the    PAT protein for achieving tolerance to the herbicide glufosinate    ammonium.-   7. NK603×MON 810 Maize from Monsanto Europe S.A. 270-272 Avenue de    Tervuren, B-1150 Brussels, Belgium, registration number    C/GB/02/M3/03. Consists of conventionally bred hybrid maize    varieties by crossing the genetically modified varieties NK603 and    MON 810. NK603×MON 810 Maize transgenically expresses the protein    CP4 EPSPS, obtained from Agrobacterium sp. strain CP4, which imparts    tolerance to the herbicide Roundup® (contains glyphosate), and also    a Cry1Ab toxin obtained from Bacillus thuringiensis subsp. kurstaki    which brings about tolerance to certain Lepidoptera, include the    European corn borer.

The term “locus” as used herein means fields in or on which plants aregrowing, or where seeds of cultivated plants are sown, or where seedwill be placed into the soil. It includes soil, seeds, and seedlings, aswell as established vegetation.

The term “plants” refers to all physical parts of a plant, includingseeds, seedlings, saplings, roots, tubers, stems, stalks, foliage, andfruits.

The term “plant propagation material” is understood to denote generativeparts of the plant, such as seeds, which can be used for themultiplication of the latter, and vegetative material, such as cuttingsor tubers, for example potatoes. There can be mentioned for exampleseeds (in the strict sense), roots, fruits, tubers, bulbs, rhizomes andparts of plants. Germinated plants and young plants which are to betransplanted after germination or after emergence from the soil, mayalso be mentioned. These young plants can be protected beforetransplantation by a total or partial treatment by immersion. Preferably“plant propagation material” is understood to denote seeds.

The compounds of formula I may be used in unmodified form or,preferably, together with the adjuvants conventionally employed in theart of formulation. To this end they may be conveniently formulated inknown manner to emulsifiable concentrates, coatable pastes, directlysprayable or dilutable solutions or suspensions, dilute emulsions,wettable powders, soluble powders, dusts, granulates, and alsoencapsulations e.g. in polymeric substances. As with the type of thecompositions, the methods of application, such as spraying, atomising,dusting, scattering, coating or pouring, are chosen in accordance withthe intended objectives and the prevailing circumstances. Thecompositions may also contain further adjuvants such as stabilizers,antifoams, viscosity regulators, binders or tackifiers as well asfertilizers, micronutrient donors or other formulations for obtainingspecial effects.

Suitable carriers and adjuvants, e.g. for agricultural use, can be solidor liquid and are substances useful in formulation technology, e.g.natural or regenerated mineral substances, solvents, dispersants,wetting agents, tackifiers, thickeners, binders or fertilizers. Suchcarriers are for example described in WO 97/33890.

Suspension concentrates are aqueous formulations in which finely dividedsolid particles of the active compound are suspended. Such formulationsinclude anti-settling agents and dispersing agents and may furtherinclude a wetting agent to enhance activity as well an anti-foam and acrystal growth inhibitor. In use, these concentrates are diluted inwater and normally applied as a spray to the area to be treated. Theamount of active ingredient may range from 0.5% to 95% of theconcentrate.

Wettable powders are in the form of finely divided particles whichdisperse readily in water or other liquid carriers. The particlescontain the active ingredient retained in a solid matrix. Typical solidmatrices include fuller's earth, kaolin clays, silicas and other readilywet organic or inorganic solids. Wettable powders normally contain from5% to 95% of the active ingredient plus a small amount of wetting,dispersing or emulsifying agent.

Emulsifiable concentrates are homogeneous liquid compositionsdispersible in water or other liquid and may consist entirely of theactive compound with a liquid or solid emulsifying agent, or may alsocontain a liquid carrier, such as xylene, heavy aromatic naphthas,isophorone and other non-volatile organic solvents. In use, theseconcentrates are dispersed in water or other liquid and normally appliedas a spray to the area to be treated. The amount of active ingredientmay range from 0.5% to 95% of the concentrate.

Granular formulations include both extrudates and relatively coarseparticles and are usually applied without dilution to the area in whichtreatment is required. Typical carriers for granular formulationsinclude sand, fuller's earth, attapulgite clay, bentonite clays,montmorillonite clay, vermiculite, perlite, calcium carbonate, brick,pumice, pyrophyllite, kaolin, dolomite, plaster, wood flour, ground corncobs, ground peanut hulls, sugars, sodium chloride, sodium sulphate,sodium silicate, sodium borate, magnesia, mica, iron oxide, zinc oxide,titanium oxide, antimony oxide, cryolite, gypsum, diatomaceous earth,calcium sulphate and other organic or inorganic materials which absorbor which can be coated with the active compound. Granular formulationsnormally contain 5% to 25% of active ingredients which may includesurface-active agents such as heavy aromatic naphthas, kerosene andother petroleum fractions, or vegetable oils; and/or stickers such asdextrins, glue or synthetic resins.

Dusts are free-flowing admixtures of the active ingredient with finelydivided solids such as talc, clays, flours and other organic andinorganic solids which act as dispersants and carriers.

Microcapsules are typically droplets or granules of the activeingredient enclosed in an inert porous shell which allows escape of theenclosed material to the surroundings at controlled rates. Encapsulateddroplets are typically 1 to 50 microns in diameter. The enclosed liquidtypically constitutes 50 to 95% of the weight of the capsule and mayinclude solvent in addition to the active compound. Encapsulatedgranules are generally porous granules with porous membranes sealing thegranule pore openings, retaining the active species in liquid forminside the granule pores. Granules typically range from 1 millimetre to1 centimetre and preferably 1 to 2 millimetres in diameter. Granules areformed by extrusion, agglomeration or prilling, or are naturallyoccurring. Examples of such materials are vermiculite, sintered clay,kaolin, attapulgite clay, sawdust and granular carbon. Shell or membranematerials include natural and synthetic rubbers, cellulosic materials,styrene-butadiene copolymers, polyacrylonitriles, polyacrylates,polyesters, polyamides, polyureas, polyurethanes and starch xanthates.

Other useful formulations for agrochemical applications include simplesolutions of the active ingredient in a solvent in which it iscompletely soluble at the desired concentration, such as acetone,alkylated naphthalenes, xylene and other organic solvents. Pressurisedsprayers, wherein the active ingredient is dispersed in finely-dividedform as a result of vaporisation of a low boiling dispersant solventcarrier, may also be used.

Suitable agricultural adjuvants and carriers that are useful informulating the compositions of the invention in the formulation typesdescribed above are well known to those skilled in the art.

Liquid carriers that can be employed include, for example, water,toluene, xylene, petroleum naphtha, crop oil, acetone, methyl ethylketone, cyclohexanone, acetic anhydride, acetonitrile, acetophenone,amyl acetate, 2-butanone, chlorobenzene, cyclohexane, cyclohexanol,alkyl acetates, diacetonalcohol, 1,2-dichloropropane, diethanolamine,p-diethylbenzene, diethylene glycol, diethylene glycol abietate,diethylene glycol butyl ether, diethylene glycol ethyl ether, diethyleneglycol methyl ether, N,N-dimethyl formamide, dimethyl sulfoxide,1,4-dioxane, dipropylene glycol, dipropylene glycol methyl ether,dipropylene glycol dibenzoate, diproxitol, alkyl pyrrolidinone, ethylacetate, 2-ethyl hexanol, ethylene carbonate, 1,1,1-trichloroethane,2-heptanone, alpha pinene, d-limonene, ethylene glycol, ethylene glycolbutyl ether, ethylene glycol methyl ether, gamma-butyrolactone,glycerol, glycerol diacetate, glycerol monoacetate, glycerol triacetate,hexadecane, hexylene glycol, isoamyl acetate, isobornyl acetate,isooctane, isophorone, isopropyl benzene, isopropyl myristate, lacticacid, laurylamine, mesityl oxide, methoxy-propanol, methyl isoamylketone, methyl isobutyl ketone, methyl laurate, methyl octanoate, methyloleate, methylene chloride, m-xylene, n-hexane, n-octylamine,octadecanoic acid, octyl amine acetate, oleic acid, oleylamine,o-xylene, phenol, polyethylene glycol (PEG400), propionic acid,propylene glycol, propylene glycol monomethyl ether, p-xylene, toluene,triethyl phosphate, triethylene glycol, xylene sulfonic acid, paraffin,mineral oil, trichloroethylene, perchloroethylene, ethyl acetate, amylacetate, butyl acetate, methanol, ethanol, isopropanol, and highermolecular weight alcohols such as amyl alcohol, tetrahydrofurfurylalcohol, hexanol, octanol, etc., ethylene glycol, propylene glycol,glycerine and N-methyl-2-pyrrolidinone. Water is generally the carrierof choice for the dilution of concentrates.

Suitable solid carriers include, for example, talc, titanium dioxide,pyrophyllite clay, silica, attapulgite clay, kieselguhr, chalk,diatomaxeous earth, lime, calcium carbonate, bentonite clay, fuller'searth, cotton seed hulls, wheat flour, soybean flour, pumice, woodflour, walnut shell flour and lignin.

A broad range of surface-active agents are advantageously employed inboth said liquid and solid compositions, especially those designed to bediluted with carrier before application. These agents, when used,normally comprise from 0.1% to 15% by weight of the formulation. Theycan be anionic, cationic, non-ionic or polymeric in character and can beemployed as emulsifying agents, wetting agents, suspending agents or forother purposes. Typical surface active agents include salts of alkylsulfates, such as diethanolammonium lauryl sulphate; alkylarylsulfonatesalts, such as calcium dodecylbenzenesulfonate; alkylphenol-alkyleneoxide addition products, such as nonylphenol-C.sub. 18 ethoxylate;alcohol-alkylene oxide addition products, such as tridecylalcohol-C.sub. 16 ethoxylate; soaps, such as sodium stearate;alkylnaphthalenesulfonate salts, such as sodiumdibutylnaphthalenesulfonate; dialkyl esters of sulfosuccinate salts,such as sodium di(2-ethylhexyl) sulfosuccinate; sorbitol esters, such assorbitol oleate; quaternary amines, such as lauryl trimethylammoniumchloride; polyethylene glycol esters of fatty acids, such aspolyethylene glycol stearate; block copolymers of ethylene oxide andpropylene oxide; and salts of mono and dialkyl phosphate esters.

Other adjuvants commonly utilized in agricultural compositions includecrystallisation inhibitors, viscosity modifiers, suspending agents,spray droplet modifiers, pigments, antioxidants, foaming agents,anti-foaming agents, light-blocking agents, compatibilizing agents,antifoam agents, sequestering agents, neutralising agents and buffers,corrosion inhibitors, dyes, odorants, spreading agents, penetrationaids, micronutrients, emollients, lubricants and sticking agents.

In addition, further, other biocidally active ingredients orcompositions may be combined with the compositions of the invention andused in the methods of the invention and applied simultaneously orsequentially with the compositions of the invention. When appliedsimultaneously, these further active ingredients may be formulatedtogether with the compositions of the invention or mixed in, forexample, the spray tank. These further biocidally active ingredients maybe fungicides, herbicides, insecticides, bactericides, acaricides,nematicides and/or plant growth regulators.

Pesticidal agents are referred to herein using their common name areknown, for example, from “The Pesticide Manual”, 15th Ed., British CropProtection Council 2009.

In addition, the compositions of the invention may also be applied withone or more systemically acquired resistance inducers (“SAR” inducer).SAR inducers are known and described in, for example, U.S. Pat. No.6,919,298 and include, for example, salicylates and the commercial SARinducer acibenzolar-S-methyl.

The compounds of formula (I) are normally used in the form ofagrochemical compositions and can be applied to the crop area or plantto be treated, simultaneously or in succession with further compounds.These further compounds can be e.g. fertilizers or micronutrient donorsor other preparations, which influence the growth of plants. They canalso be selective herbicides or non-selective herbicides as well asinsecticides, fungicides, bactericides, nematicides, molluscicides ormixtures of several of these preparations, if desired together withfurther carriers, surfactants or application promoting adjuvantscustomarily employed in the art of formulation.

The compounds of formula (I) may be used in the form of (fungicidal)compositions for controlling or protecting against phytopathogenicmicroorganisms, comprising as active ingredient at least one compound offormula (I) or of at least one preferred individual compound as definedherein, in free form or in agrochemically usable salt form, and at leastone of the above-mentioned adjuvants.

The invention therefore provides a composition, preferably a fungicidalcomposition, comprising at least one compound formula (I) anagriculturally acceptable carrier and optionally an adjuvant. Anagricultural acceptable carrier is for example a carrier that issuitable for agricultural use. Agricultural carriers are well known inthe art. Preferably said composition may comprise at least one or morepesticidally-active compounds, for example an additional fungicidalactive ingredient in addition to the compound of formula (I).

The compound of formula (I) may be the sole active ingredient of acomposition or it may be admixed with one or more additional activeingredients such as a pesticide, fungicide, synergist, herbicide orplant growth regulator where appropriate. An additional activeingredient may, in some cases, result in unexpected synergisticactivities.

Examples of suitable additional active ingredients include thefollowing: acycloamino acid fungicides, aliphatic nitrogen fungicides,amide fungicides, anilide fungicides, antibiotic fungicides, aromaticfungicides, arsenical fungicides, aryl phenyl ketone fungicides,benzamide fungicides, benzanilide fungicides, benzimidazole fungicides,benzothiazole fungicides, botanical fungicides, bridged diphenylfungicides, carbamate fungicides, carbanilate fungicides, conazolefungicides, copper fungicides, dicarboximide fungicides, dinitrophenolfungicides, dithiocarbamate fungicides, dithiolane fungicides, furamidefungicides, furanilide fungicides, hydrazide fungicides, imidazolefungicides, mercury fungicides, morpholine fungicides, organophosphorousfungicides, organotin fungicides, oxathiin fungicides, oxazolefungicides, phenylsulfamide fungicides, polysulfide fungicides, pyrazolefungicides, pyridine fungicides, pyrimidine fungicides, pyrrolefungicides, quaternary ammonium fungicides, quinoline fungicides,quinone fungicides, quinoxaline fungicides, strobilurin fungicides,sulfonanilide fungicides, thiadiazole fungicides, thiazole fungicides,thiazolidine fungicides, thiocarbamate fungicides, thiophene fungicides,triazine fungicides, triazole fungicides, triazolopyrimidine fungicides,urea fungicides, valinamide fungicides, and zinc fungicides.

Examples of suitable additional active ingredients also include thefollowing: 3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acid(9-dichloromethylene-1,2,3,4-tetrahydro-1,4-methano-naphthalen-5-yl)-amide,3-difluoromethyl-1-methyl-1H-pyrazole-4-carboxylic acidmethoxy-[1-methyl-2-(2,4,6-trichlorophenyl)-ethyl]-amide,1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid(2-dichloromethylene-3-ethyl-1-methyl-indan-4-yl)-amide (1072957-71-1),1-methyl-3-difluoromethyl-1H-pyrazole-4-carboxylic acid(4′-methylsulfanyl-biphenyl-2-yl)-amide,1-methyl-3-difluoromethyl-4H-pyrazole-4-carboxylic acid[2-(2,4-dichloro-phenyl)-2-methoxy-1-methyl-ethyl]amide,(5-chloro-2,4-dimethyl-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone,(5-Bromo-4-chloro-2-methoxy-pyridin-3-yl)-(2,3,4-trimethoxy-6-methyl-phenyl)-methanone,2-{2-[(E)-3-(2,6-Dichloro-phenyl)-1-methyl-prop-2-en-(E)-ylideneaminooxymethyl]-phenyl}-2-[(Z)-methoxyimino]-N-methyl-acetamide,3-[5-(4-chloro-phenyl)-2,3-dimethyl-isoxazolidin-3-yl]-pyridine,(E)-N-methyl-2-[2-(2,5-dimethylphenoxymethyl)phenyl]-2-methoxy-iminoacetamide,4-bromo-2-cyano-N,N-dimethyl-6-trifluoromethylbenzimidazole-1-sulphonamide,a-[N-(3-chloro-2,6-xylyl)-2-methoxyacetamido]-y-butyrolactone,4-chloro-2-cyano-N,-dimethyl-5-p-tolylimidazole-1-sulfonamide,N-allyl-4,5,-dimethyl-2-trimethylsilylthiophene-3-carboxamide,N-(I-cyano-1,2-dimethylpropyl)-2-(2,4-dichlorophenoxy) propionamide,N-(2-methoxy-5-pyridyl)-cyclopropane carboxamide,(.+-.)-cis-1-(4-chlorophenyl)-2-(1H-1,2,4-triazol-1-yl)-cycloheptanol,2-(1-tert-butyl)-1-(2-chlorophenyl)-3-(1,2,4-triazol-1-yl)-propan-2-ol,2′,6′-dibromo-2-methyl-4-trifluoromethoxy-4′-trifluoromethyl-1,3-thiazole-5-carboxanilide,1-imidazolyl-1-(4′-chlorophenoxy)-3,3-dimethylbutan-2-one, methyl(E)-2-[2-[6-(2-cyanophenoxy)pyrimidin-4-yloxy]phenyl]3-methoxyacrylate,methyl(E)-2-[2-[6-(2-thioamidophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-fluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2,6-difluorophenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl (E)-2-[2-[3-(pyrimidin-2-yloxy)phenoxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[3-(5-methylpyrimidin-2-yloxy)-phenoxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[3-(phenyl-sulphonyloxy)phenoxy]phenyl-3-methoxyacrylate,methyl (E)-2-[2-[3-(4-nitrophenoxy)phenoxy]phenyl]-3-methoxyacrylate,methyl (E)-2-[2-phenoxyphenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dimethyl-benzoyl)pyrrol-1-yl]-3-methoxyacrylate, methyl(E)-2-[2-(3-methoxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(2-phenylethen-1-yl)-phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3,5-dichlorophenoxy)pyridin-3-yl]-3-methoxyacrylate, methyl(E)-2-(2-(3-(1,1,2,2-tetrafluoroethoxy)phenoxy)phenyl)-3-methoxyacrylate,methyl(E)-2-(2-[3-(alpha-hydroxybenzyl)phenoxy]phenyl)-3-methoxyacrylate,methyl (E)-2-(2-(4-phenoxypyridin-2-yloxy)phenyl)-3-methoxyacrylate,methyl (E)-2-[2-(3-n-propyloxy-phenoxy)phenyl]3-methoxyacrylate, methyl(E)-2-[2-(3-isopropyloxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(2-fluorophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(3-ethoxyphenoxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-(4-tert-butyl-pyridin-2-yloxy)phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[3-(3-cyanophenoxy)phenoxy]phenyl]-3-methoxyacrylate, methyl(E)-2-[2-[(3-methyl-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-methyl-phenoxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E)-2-[2-(5-bromo-pyridin-2-yloxymethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-(3-(3-iodopyridin-2-yloxy)phenoxy)phenyl]-3-methoxyacrylate,methyl(E)-2-[2-[6-(2-chloropyridin-3-yloxy)pyrimidin-4-yloxy]phenyl]-3-methoxyacrylate,methyl(E),(E)-2-[2-(5,6-dimethylpyrazin-2-ylmethyloxy)iminomethyl)phenyl]-3-methoxyacrylate,methyl(E)-2-{2-[6-(6-methylpyridin-2-yloxy)pyrimidin-4-yloxy]phenyl}-3-methoxy-acrylate,methyl(E),(E)-2-{2-(3-methoxyphenyl)methyloximinomethyl]-phenyl}-3-methoxyacrylate,methyl(E)-2-{2-(6-(2-azidophenoxy)-pyrimidin-4-yloxy]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[6-phenylpyrimidin-4-yl)-methyloximinomethyl]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[(4-chlorophenyl)-methyloximinomethyl]-phenyl}-3-methoxyacrylate,methyl(E)-2-{2-[6-(2-n-propylphenoxy)-1,3,5-triazin-4-yloxy]phenyl}-3-methoxyacrylate,methyl(E),(E)-2-{2-[(3-nitrophenyl)methyloximinomethyl]phenyl}-3-methoxyacrylate,3-chloro-7-(2-aza-2,7,7-trimethyl-oct-3-en-5-ine),2,6-dichloro-N-(4-trifluoromethylbenzyl)-benzamide, 3-iodo-2-propinylalcohol, 4-chlorophenyl-3-iodopropargyl formal,3-bromo-2,3-diiodo-2-propenyl ethylcarbamate, 2,3,3-triiodoallylalcohol, 3-bromo-2,3-diiodo-2-propenyl alcohol, 3-iodo-2-propinyln-butylcarbamate, 3-iodo-2-propinyl n-hexylcarbamate, 3-iodo-2-propinylcyclohexyl-carbamate, 3-iodo-2-propinyl phenylcarbamate; phenolderivatives, such as tribromophenol, tetrachlorophenol,3-methyl-4-chlorophenol, 3,5-dimethyl-4-chlorophenol, phenoxyethanol,dichlorophene, o-phenylphenol, m-phenylphenol, p-phenylphenol,2-benzyl-4-chlorophenol, 5-hydroxy-2(5H)-furanone;4,5-dichlorodithiazolinone, 4,5-benzodithiazolinone,4,5-trimethylenedithiazolinone, 4,5-dichloro-(3H)-1,2-dithiol-3-one,3,5-dimethyl-tetrahydro-1,3,5-thiadiazine-2-thione,N-(2-p-chlorobenzoylethyl)-hexaminium chloride, acibenzolar, acypetacs,alanycarb, albendazole, aldimorph, allicin, allyl alcohol, ametoctradin,amisulbrom, amobam, ampropylfos, anilazine, asomate, aureofungin,azaconazole, azafendin, azithiram, azoxystrobin, barium polysulfide,benalaxyl, benalaxyl-M, benodanil, benomyl, benquinox, bentaluron,benthiavalicarb, benthiazole, benzalkonium chloride, benzamacril,benzamorf, benzohydroxamic acid, benzovindiflupyr, berberine,bethoxazin, biloxazol, binapacryl, biphenyl, bitertanol, bithionol,bixafen, blasticidin-S, boscalid, bromothalonil, bromuconazole,bupirimate, buthiobate, butylamine calcium polysulfide, captafol,captan, carbamorph, carbendazim, carbendazim chlorhydrate, carboxin,carpropamid, carvone, CGA41396, CGA41397, chinomethionate, chitosan,chlobenthiazone, chloraniformethan, chloranil, chlorfenazole, chloroneb,chloropicrin, chlorothalonil, chlorozolinate, chlozolinate, climbazole,clotrimazole, clozylacon, copper containing compounds such as copperacetate, copper carbonate, copper hydroxide, copper naphthenate, copperoleate, copper oxychloride, copper oxyquinolate, copper silicate, coppersulphate, copper tallate, copper zinc chromate and Bordeaux mixture,cresol, cufraneb, cuprobam, cuprous oxide, cyazofamid, cyclafuramid,cycloheximide, cyflufenamid, cymoxanil, cypendazole, cyproconazole,cyprodinil, dazomet, debacarb, decafentin, dehydroacetic acid,di-2-pyridyl disulphide 1,1′-dioxide, dichlofluanid, diclomezine,dichlone, dicloran, dichlorophen, dichlozoline, diclobutrazol,diclocymet, diethofencarb, difenoconazole, difenzoquat, diflumetorim, O,O-di-iso-propyl-S-benzyl thiophosphate, dimefluazole, dimetachlone,dimetconazole, dimethomorph, dimethirimol, diniconazole, diniconazole-M,dinobuton, dinocap, dinocton, dinopenton, dinosulfon, dinoterbon,diphenylamine, dipyrithione, disulfiram, ditalimfos, dithianon,dithioether, dodecyl dimethyl ammonium chloride, dodemorph, dodicin,dodine, doguadine, drazoxolon, edifenphos, enestroburin, epoxiconazole,etaconazole, etem, ethaboxam, ethirimol, ethoxyquin, ethilicin, ethyl(Z)—N-benzyl-N ([methyl(methyl-thioethylideneamino-oxycarbonyl)amino]thio)-β-alaninate, etridiazole, famoxadone, fenamidone,fenaminosulf, fenapanil, fenarimol, fenbuconazole, fenfuram, fenhexamid,fenitropan, fenoxanil, fenpiclonil, fenpropidin, fenpropimorph,fenpyrazamine, fentin acetate, fentin hydroxide, ferbam, ferimzone,fluazinam, fludioxonil, flumetover, flumorph, flupicolide, fluopyram,fluoroimide, fluotrimazole, fluoxastrobin, fluquinconazole, flusilazole,flusulfamide, flutanil, flutolanil, flutriafol, fluxapyroxad, folpet,formaldehyde, fosetyl, fuberidazole, furalaxyl, furametpyr, furcarbanil,furconazole, furfural, furmecyclox, furophanate, glyodin, griseofulvin,guazatine, halacrinate, hexa chlorobenzene, hexachlorobutadiene,hexachlorophene, hexaconazole, hexylthiofos, hydrargaphen,hydroxyisoxazole, hymexazole, imazalil, imazalil sulphate,imibenconazole, iminoctadine, iminoctadine triacetate, inezin, iodocarb,ipconazole, ipfentrifluconazole, iprobenfos, iprodione, iprovalicarb,isopropanyl butyl carbamate, isoprothiolane, isopyrazam, isotianil,isovaledione, izopamfos, kasugamycin, kresoxim-methyl, LY186054,LY211795, LY248908, mancozeb, mandipropamid, maneb, mebenil,mecarbinzid, mefenoxam, mefentrifluconazole, mepanipyrim, mepronil,mercuric chloride, mercurous chloride, meptyldinocap, metalaxyl,metalaxyl-M, metam, metazoxolon, metconazole, methasulfocarb,methfuroxam, methyl bromide, methyl iodide, methyl isothiocyanate,metiram, metiram-zinc, metominostrobin, metrafenone, metsulfovax,milneb, moroxydine, myclobutanil, myclozolin, nabam, natamycin,neoasozin, nickel dimethyldithiocarbamate, nitrostyrene,nitrothal-iso-propyl, nuarimol, octhilinone, ofurace, organomercurycompounds, orysastrobin, osthol, oxadixyl, oxasulfuron, oxine-copper,oxolinic acid, oxpoconazole, oxycarboxin, parinol, pefurazoate,penconazole, pencycuron, penflufen, pentachlorophenol, penthiopyrad,phenamacril, phenazin oxide, phosdiphen, phosetyl-Al, phosphorus acids,phthalide, picoxystrobin, piperalin, polycarbamate, polyoxin D,polyoxrim, polyram, probenazole, prochloraz, procymidone, propamidine,propamocarb, propiconazole, propineb, propionic acid, proquinazid,prothiocarb, prothioconazole, pydiflumetofen, pyracarbolid,pyraclostrobin, pyrametrostrobin, pyraoxystrobin, pyrazophos,pyribencarb, pyridinitril, pyrifenox, pyrimethanil, pyriofenone,pyroquilon, pyroxychlor, pyroxyfur, pyrrolnitrin, quaternary ammoniumcompounds, quinacetol, quinazamid, quinconazole, quinomethionate,quinoxyfen, quintozene, rabenzazole, santonin, sedaxane, silthiofam,simeconazole, sipconazole, sodium pentachlorophenate, solatenol,spiroxamine, streptomycin, sulphur, sultropen, tebuconazole, tebfloquin,tecloftalam, tecnazene, tecoram, tetraconazole, thiabendazole,thiadifluor, thicyofen, thifluzamide, 2-(thiocyanomethylthio)benzothiazole, thiophanate-methyl, thioquinox, thiram, tiadinil,timibenconazole, tioxymid, tolclofos-methyl, tolylfluanid, triadimefon,triadimenol, triamiphos, triarimol, triazbutil, triazoxide,tricyclazole, tridemorph, trifloxystrobin, triflumazole, triforine,triflumizole, triticonazole, uniconazole, urbacide, validamycin,valifenalate, vapam, vinclozolin, zarilamid, zineb, ziram, and zoxamide.

The compounds of the invention may also be used in combination withanthelmintic agents. Such anthelmintic agents include, compoundsselected from the macrocyclic lactone class of compounds such asivermectin, avermectin, abamectin, emamectin, eprinomectin, doramectin,selamectin, moxidectin, nemadectin and milbemycin derivatives asdescribed in EP-357460, EP-444964 and EP-594291. Additional anthelminticagents include semisynthetic and biosynthetic avermectin/milbemycinderivatives such as those described in US-5015630, WO-9415944 andWO-9522552. Additional anthelmintic agents include the benzimidazolessuch as albendazole, cambendazole, fenbendazole, flubendazole,mebendazole, oxfendazole, oxibendazole, parbendazole, and other membersof the class. Additional anthelmintic agents include imidazothiazolesand tetrahydropyrimidines such as tetramisole, levamisole, pyrantelpamoate, oxantel or morantel. Additional anthelmintic agents includeflukicides, such as triclabendazole and clorsulon and the cestocides,such as praziquantel and epsiprantel.

The compounds of the invention may be used in combination withderivatives and analogues of the paraherquamide/marcfortine class ofanthelmintic agents, as well as the antiparasitic oxazolines such asthose disclosed in U.S. Pat. Nos. 5,478,855, 4,639,771 and DE-19520936.

The compounds of the invention may be used in combination withderivatives and analogues of the general class of dioxomorpholineantiparasitic agents as described in WO 96/15121 and also withanthelmintic active cyclic depsipeptides such as those described in WO96/11945, WO 93/19053, WO 93/25543, EP 0 626 375, EP 0 382 173, WO94/19334, EP 0 382 173, and EP 0 503 538.

The compounds of the invention may be used in combination with otherectoparasiticides; for example, fipronil; pyrethroids; organophosphates;insect growth regulators such as lufenuron; ecdysone agonists such astebufenozide and the like; neonicotinoids such as imidacloprid and thelike.

The compounds of the invention may be used in combination with terpenealkaloids, for example those described in International PatentApplication Publication Numbers WO 95/19363 or WO 04/72086, particularlythe compounds disclosed therein.

Other examples of such biologically active compounds that the compoundsof the invention may be used in combination with include but are notrestricted to the following:

Organophosphates: acephate, azamethiphos, azinphos-ethyl,azinphos-methyl, bromophos, bromophos-ethyl, cadusafos, chlorethoxyphos,chlorpyrifos, chlorfenvinphos, chlormephos, demeton, demeton-S-methyl,demeton-S-methyl sulphone, dialifos, diazinon, dichlorvos, dicrotophos,dimethoate, disulfoton, ethion, ethoprophos, etrimfos, famphur,fenamiphos, fenitrothion, fensulfothion, fenthion, flupyrazofos,fonofos, formothion, fosthiazate, heptenophos, isazophos, isothioate,isoxathion, malathion, methacriphos, methamidophos, methidathion,methyl-parathion, mevinphos, monocrotophos, naled, omethoate,oxydemeton-methyl, paraoxon, parathion, parathion-methyl, phenthoate,phosalone, phosfolan, phosphocarb, phosmet, phosphamidon, phorate,phoxim, pirimiphos, pirimiphos-methyl, profenofos, propaphos,proetamphos, prothiofos, pyraclofos, pyridapenthion, quinalphos,sulprophos, temephos, terbufos, tebupirimfos, tetrachlorvinphos,thimeton, triazophos, trichlorfon, vamidothion.

Carbamates: alanycarb, aldicarb, 2-sec-butylphenyl methylcarbamate,benfuracarb, carbaryl, carbofuran, carbosulfan, cloethocarb,ethiofencarb, fenoxycarb, fenthiocarb, furathiocarb, HCN-801,isoprocarb, indoxacarb, methiocarb, methomyl,5-methyl-m-cumenylbutyryl(methyl)carbamate, oxamyl, pirimicarb,propoxur, thiodicarb, thiofanox, triazamate, UC-51717.

Pyrethroids: acrinathin, allethrin, alphametrin, 5-benzyl-3-furylmethyl(E)-(1R)-cis-2,2-dimethyl-3-(2-oxothiolan-3-ylidenemethyl)cyclopropanecarboxylate,bifenthrin, beta-cyfluthrin, cyfluthrin, a-cypermethrin,beta-cypermethrin, bioallethrin, bioallethrin((S)-cyclopentylisomer),bioresmethrin, bifenthrin, NCI-85193, cycloprothrin, cyhalothrin,cythithrin, cyphenothrin, deltamethrin, empenthrin, esfenvalerate,ethofenprox, fenfluthrin, fenpropathrin, fenvalerate, flucythrinate,flumethrin, fluvalinate (D isomer), imiprothrin, cyhalothrin,lambda-cyhalothrin, permethrin, phenothrin, prallethrin, pyrethrins(natural products), resmethrin, tetramethrin, transfluthrin,theta-cypermethrin, silafluofen, t-fluvalinate, tefluthrin,tralomethrin, Zeta-cypermethrin.

Arthropod growth regulators: a) chitin synthesis inhibitors:benzoylureas: chlorfluazuron, diflubenzuron, fluazuron, flucycloxuron,flufenoxuron, hexaflumuron, lufenuron, novaluron, teflubenzuron,triflumuron, buprofezin, diofenolan, hexythiazox, etoxazole,chlorfentazine; b) ecdysone antagonists: halofenozide, methoxyfenozide,tebufenozide; c) juvenoids: pyriproxyfen, methoprene (includingS-methoprene), fenoxycarb; d) lipid biosynthesis inhibitors:spirodiclofen.

Other antiparasitics: acequinocyl, amitraz, AKD-1022, ANS-118,azadirachtin, Bacillus thuringiensis, bensultap, bifenazate, binapacryl,bromopropylate, BTG-504, BTG-505, camphechlor, cartap, chlorobenzilate,chlordimeform, chlorfenapyr, chromafenozide, clothianidine, cyromazine,diacloden, diafenthiuron, DBI-3204, dinactin,dihydroxymethyldihydroxypyrrolidine, dinobuton, dinocap, endosulfan,ethiprole, ethofenprox, fenazaquin, flumite, MTI-800, fenpyroximate,fluacrypyrim, flubenzimine, flubrocythrinate, flufenzine, flufenprox,fluproxyfen, halofenprox, hydramethylnon, IKI-220, kanemite, NC-196,neem guard, nidinorterfuran, nitenpyram, SD-35651, WL-108477, pirydaryl,propargite, protrifenbute, pymethrozine, pyridaben, pyrimidifen,NC-1111, R-195, RH-0345, RH-2485, RYI-210, S-1283, S-1833, S1-8601,silafluofen, silomadine, spinosad, tebufenpyrad, tetradifon,tetranactin, thiacloprid, thiocyclam, thiamethoxam, tolfenpyrad,triazamate, triethoxyspinosyn, trinactin, verbutin, vertalec, YI-5301.

Biological agents: Bacillus thuringiensis ssp aizawai, kurstaki,Bacillus thuringiensis delta endotoxin, baculovirus, entomopathogenicbacteria, virus and fungi.

Bactericides: chlortetracycline, oxytetracycline, streptomycin.

Other biological agents: enrofloxacin, febantel, penethamate, moloxicam,cefalexin, kanamycin, pimobendan, clenbuterol, omeprazole, tiamulin,benazepril, pyriprole, cefquinome, florfenicol, buserelin, cefovecin,tulathromycin, ceftiour, carprofen, metaflumizone, praziquarantel,triclabendazole.

Another aspect of invention is related to the use of a compound offormula (I) or of a preferred individual compound as defined herein, ofa composition comprising at least one compound of formula (I) or atleast one preferred individual compound as above-defined, or of afungicidal or insecticidal mixture comprising at least one compound offormula (I) or at least one preferred individual compound asabove-defined, in admixture with other fungicides or insecticides asdescribed above, for controlling or preventing infestation of plants,e.g. useful plants such as crop plants, propagation material thereof,e.g. seeds, harvested crops, e.g. harvested food crops, or non-livingmaterials by insects or by phytopathogenic microorganisms, preferablyfungal organisms.

A further aspect of invention is related to a method of controlling orpreventing an infestation of plants, e.g., useful plants such as cropplants, propagation material thereof, e.g. seeds, harvested crops, e.g.,harvested food crops, or of non-living materials by insects or byphytopathogenic or spoilage microorganisms or organisms potentiallyharmful to man, especially fungal organisms, which comprises theapplication of a compound of formula (I) or of a preferred individualcompound as above-defined as active ingredient to the plants, to partsof the plants or to the locus thereof, to the propagation materialthereof, or to any part of the non-living materials.

Controlling or preventing means reducing infestation by phytopathogenicor spoilage microorganisms or organisms potentially harmful to man,especially fungal organisms, to such a level that an improvement isdemonstrated.

A preferred method of controlling or preventing an infestation of cropplants by phytopathogenic microorganisms, especially fungal organisms,or insects which comprises the application of a compound of formula (I),or an agrochemical composition which contains at least one of saidcompounds, is foliar application. The frequency of application and therate of application will depend on the risk of infestation by thecorresponding pathogen or insect. However, the compounds of formula (I)can also penetrate the plant through the roots via the soil (systemicaction) by drenching the locus of the plant with a liquid formulation,or by applying the compounds in solid form to the soil, e.g. in granularform (soil application). In crops of water rice such granulates can beapplied to the flooded rice field. The compounds of formula I may alsobe applied to seeds (coating) by impregnating the seeds or tubers eitherwith a liquid formulation of the fungicide or coating them with a solidformulation.

A formulation, e.g. a composition containing the compound of formula(I), and, if desired, a solid or liquid adjuvant or monomers forencapsulating the compound of formula (I), may be prepared in a knownmanner, typically by intimately mixing and/or grinding the compound withextenders, for example solvents, solid carriers and, optionally, surfaceactive compounds (surfactants).

Advantageous rates of application are normally from 5 g to 2 kg ofactive ingredient (a.i.) per hectare (ha), preferably from 10 g to 1 kga.i./ha, most preferably from 20 g to 600 g a.i./ha. When used as seeddrenching agent, convenient dosages are from 10 mg to 1 g of activesubstance per kg of seeds.

When the combinations of the present invention are used for treatingseed, rates of 0.001 to 50 g of a compound of formula I per kg of seed,preferably from 0.01 to 10 g per kg of seed are generally sufficient.

Suitably, a composition comprising a compound of formula (I) accordingto the present invention is applied either preventative, meaning priorto disease development or curative, meaning after disease development.

The compositions of the invention may be employed in any conventionalform, for example in the form of a twin pack, a powder for dry seedtreatment (DS), an emulsion for seed treatment (ES), a flowableconcentrate for seed treatment (FS), a solution for seed treatment (LS),a water dispersible powder for seed treatment (WS), a capsule suspensionfor seed treatment (CF), a gel for seed treatment (GF), an emulsionconcentrate (EC), a suspension concentrate (SC), a suspo-emulsion (SE),a capsule suspension (CS), a water dispersible granule (WG), anemulsifiable granule (EG), an emulsion, water in oil (EO), an emulsion,oil in water (EW), a micro-emulsion (ME), an oil dispersion (OD), an oilmiscible flowable (OF), an oil miscible liquid (OL), a solubleconcentrate (SL), an ultra-low volume suspension (SU), an ultra-lowvolume liquid (UL), a technical concentrate (TK), a dispersibleconcentrate (DC), a wettable powder (WP) or any technically feasibleformulation in combination with agriculturally acceptable adjuvants.

Such compositions may be produced in conventional manner, e.g. by mixingthe active ingredients with appropriate formulation inerts (diluents,solvents, fillers and optionally other formulating ingredients such assurfactants, biocides, anti-freeze, stickers, thickeners and compoundsthat provide adjuvancy effects). Also conventional slow releaseformulations may be employed where long lasting efficacy is intended.Particularly formulations to be applied in spraying forms, such as waterdispersible concentrates (e.g. EC, SC, DC, OD, SE, EW, EO and the like),wettable powders and granules, may contain surfactants such as wettingand dispersing agents and other compounds that provide adjuvancyeffects, e.g. the ondensation product of formaldehyde with naphthalenesulphonate, an alkylarylsulphonate, a lignin sulphonate, a fatty alkylsulphate, and ethoxylated alkylphenol and an ethoxylated fatty alcohol.

A seed dressing formulation is applied in a manner known per se to theseeds employing the combination of the invention and a diluent insuitable seed dressing formulation form, e.g. as an aqueous suspensionor in a dry powder form having good adherence to the seeds. Such seeddressing formulations are known in the art. Seed dressing formulationsmay contain the single active ingredients or the combination of activeingredients in encapsulated form, e.g. as slow release capsules ormicrocapsules.

In general, the formulations include from 0.01 to 90% by weight ofactive agent, from 0 to 20% agriculturally acceptable surfactant and 10to 99.99% solid or liquid formulation inerts and adjuvant(s), the activeagent consisting of at least the compound of formula (I) optionallytogether with other active agents, particularly microbiocides orconservatives or the like. Concentrated forms of compositions generallycontain in between about 2 and 80%, preferably between about 5 and 70%by weight of active agent. Application forms of formulation may forexample contain from 0.01 to 20% by weight, preferably from 0.01 to 5%by weight of active agent. Whereas commercial products will preferablybe formulated as concentrates, the end user will normally employ dilutedformulations.

Whereas, it is preferred to formulate commercial products asconcentrates, the end user will normally use dilute formulations.

-   Table 1.1: This table discloses 149 specific compounds of the    formula (T-1):

wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹,R², R³, R⁴, R⁵ and R⁶ are hydrogen, R⁷ is methoxy and R⁸ is as definedbelow in the Table 1.

Each of Tables 1.2 to 1.29 (which follow Table 1.1) make available 149individual compounds of the formula (T-1) in which n, A¹, A², A³, A⁴,R¹, R², R³, R⁴, R⁵, R⁶, and R⁷ are as specifically defined in Tables 1.2to 1.29, which refer to Table 1 wherein R⁸ is specifically defined.

TABLE 1 Compound no. R⁸ 1.001 methyl 1.002 ethyl 1.003 propyl 1.004isopropyl 1.005 butyl 1.006 sec-butyl 1.007 2-methylbutyl 1.008tert-butyl 1.009 isobutyl 1.010 pentyl 1.011 1-ethylpropyl 1.0122-ethylbutyl 1.013 2,2-dimethylpropyl 1.014 1,1-dimethylbutyl 1.0152,2-dimethylbutyl 1.016 1-ethyl-1-methylpropyl 1.017 but-2-enyl 1.0182-methylpropenyl 1.019 ethenyl 1.020 propen-2-yl 1.021 allyl 1.0221-methylallyl 1.023 2-methylallyl 1.024 1,1-dimethylallyl 1.0251-methylprop-1-enyl 1.026 but-1-enyl 1.027 3-methylbut-2-enyl 1.028(E)-1,1-dimethylbut-2-enyl 1.029 but-3-enyl 1.030 prop-2-ynyl 1.031but-3-ynyl 1.032 but-2-ynyl 1.033 1-methylprop-2-ynyl 1.0341-methylbut-2-ynyl 1.035 1,1-dimethylprop-2-ynyl 1.036 cyanomethyl 1.0372-cyanoethyl 1.038 3-cyanopropyl 1.039 1-ethoxymethyl 1.0401-methoxymethyl 1.041 difluoromethoxymethyl 1.042 1-difluoromethoxyethyl1.043 1-methoxyethyl 1.044 1-methoxyisopropyl 1.045 1-ethyloxyisopropyl1.046 1-difluoromethoxyisopropyl 1.047 2-methoxyethyl 1.0482-(difluoromethoxy)ethyl 1.049 3-methoxypropyl 1.050 4-methoxybutyl1.051 2-ethoxyethyl 1.052 1-ethoxyethyl 1.053 2-methoxypropyl 1.0541-(methoxymethyl)propyl 1.055 2-methoxy-1,1-dimethyl-ethyl 1.0562-methoxyethoxymethyl 1.057 1-acetoxymethyl 1.058 2-acetoxyethyl 1.0592-acetoxy-1,1-dimethyl-ethyl 1.060 2,2-diethoxyethyl 1.0612,2-dimethoxyethyl 1.062 hydroxymethyl 1.063 1-hydroxyethyl 1.0641-hydroxyisopropyl 1.065 2-hydroxyethyl 1.066 2-hydroxypropyl 1.0673-hydroxypropyl 1.068 2-hydroxy-1,1-dimethyl-ethyl 1.0692-hydroxy-2-methyl-propyl 1.070 trifluoromethyl 1.0712,2,2-trifluoroethyl 1.072 3,3,3-trifluoropropyl 1.0734,4,4-trifluorobutyl 1.074 fluoromethyl 1.075 difluoromethyl 1.0762-fluoroethyl 1.077 1-fluoroethyl 1.078 chloromethyl 1.079 2-chloroethyl1.080 2-chloro-1,1-dimethylethyl 1.081 2-(methylamino)-2-oxo-ethyl 1.0822-(ethylamino)-2-oxo-ethyl 1.083 2-(tert-butylamino)-2-oxo-ethyl 1.0842-(isopropylamino)-2-oxo-ethyl 1.085 acetamidomethyl 1.086acetamidoethyl 1.087 1-methyl-3-oxo-butyl 1.0883-methoxy-1-methyl-3-oxo-propyl 1.089 3-methoxy-3-oxo-propyl 1.090phenyl 1.091 2-chlorophenyl 1.092 2-fluorophenyl 1.093 3-fluorophenyl1.094 4-fluorophenyl 1.095 3,5-difluorophenyl 1.096 4-pyrimidinyl 1.097thiazol-5-yl 1.098 oxazol-5-yl 1.099 isoxazol-3-yl 1.100 2-pyridyl 1.101benzyl 1.102 3-chlorophenylmethyl 1.103 3-fluorophenylmethyl 1.1042-pyridylmethyl 1.105 cyclopentyl 1.106 cyclohexyl 1.107cyclopentylmethyl 1.108 cyclohexylmethyl 1.109 cyclopropylmethyl 1.110cyclopropyl 1.111 1-chlorocycloprop-1-yl 1.112 1-cyanocycloprop-1-yl1.113 1-fluorocycloprop-1-yl 1.114 1-methylcyclopropyl 1.1151-trifluoromethylcycloprop-1-yl 1.116 2-cyanocyclopropyl 1.1172-fluorocyclopropyl 1.118 2-methylcyclopropyl 1.1192,2-dichlorocyclopropyl 1.120 2,2-difluorocyclopropyl 1.1212,2-dimethylcyclopropyl 1.122 2,2,3,3-tetramethylcyclopropyl 1.1232,2-dichloro-1-methyl-cyclopropyl 1.124 cyclobutyl 1.1251-methylcyclobutyl 1.126 1-(trifluoromethyl)cyclobutyl 1.1271-cyanocyclobut-1-yl 1.128 cyclobutylmethyl 1.1292,2-difluorocyclopropylmethyl 1.130 tetrahydrothiopyran-2-yl 1.131tetrahydrothiopyran-3-yl 1.132 tetrahydrothiopyran-4-yl 1.133oxetan-3-yl 1.134 3-cyanooxetan-3-yl 1.135 3-methyloxetan-3-yl 1.1363-trifluoromethyloxetan-3-yl 1.137 oxetan-2-yl 1.138 oxetan-3-ylmethyl1.139 oxetan-2-ylmethyl 1.140 tetrahydrofuran-2-yl 1.141tetrahydrofuran-3-yl 1.142 tetrahydrofuran-2-ylmethyl 1.143tetrahydropyran-2-yl 1.144 tetrahydropyran-3-yl 1.145tetrahydropyran-4-yl 1.146 2-methyl-1,3-dioxolan-2-yl 1.1471,3-dioxolan-2-yl 1.148 1-acetylpyrrolidin-2-yl 1.149 1-imidazoyl

-   Table 1.2: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is methoxy, R¹ is    fluorine, and R⁸ is as defined above in Table 1.-   Table 1.3: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is methoxy, R¹ is    chlorine, and R⁸ is as defined above in Table 1.-   Table 1.4: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is methoxy, R¹ is    methyl, and R⁸ is as defined above in Table 1.-   Table 1.5: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is N, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is methoxy, and R⁸ is as    defined above in Table 1.-   Table 1.6: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R⁴, R⁵, and R⁶ are hydrogen, R⁷ is methoxy, R³ is    fluorine, and R⁸ is as defined above in Table 1.-   Table 1.7: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R², R⁴, R⁵, and R⁶ are hydrogen, R⁷ is methoxy, R¹ and R³ are    fluorine, and R⁸ is as defined above in Table 1.-   Table 1.8: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is methoxy, R¹ and R² are    fluorine, and R⁸ is as defined above in Table 1.-   Table 1.9: This table discloses 149 specific compounds of formula    (T-1) wherein n is 2, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is methoxy, and R⁸    is as defined above in Table 1.-   Table 1.10: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, and R⁵ are hydrogen, R⁷ is methoxy, R⁶ is    methyl, and R⁸ is as defined above in Table 1.-   Table 1.11: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³ R⁴, and R⁵ are hydrogen, R⁷ is methyl, R⁶ is cyano,    and R⁸ is as defined above in Table 1.-   Table 1.13: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is methyl, and R⁸ is    as defined above in Table 1.-   Table 1.14: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is ethyl, and R⁸ is    as defined above in Table 1.-   Table 1.15: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is propyl, and R⁸ is    as defined above in Table 1.-   Table 1.16: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is isopropyl, and R⁸    is as defined above in Table 1.-   Table 1.17: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is allyl, and R⁸ is    as defined above in Table 1.-   Table 1.18: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is isobutyl, and R⁸    is as defined above in Table 1.-   Table 1.19: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is 2-methoxyethyl,    and R⁸ is as defined above in Table 1.-   Table 1.20: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is propyloxy, and R⁸    is as defined above in Table 1.-   Table 1.21: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is 2-propynl, and R⁸    is as defined above in Table 1.-   Table 1.22: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is 2-furylmethyl,    and R⁸ is as defined above in Table 1.-   Table 1.23: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is    tetrahydrofuran-2-ylmethyl, and R⁸ is as defined above in Table 1.-   Table 1.24: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is    cyclopropylmethyl, and R⁸ is as defined above in Table 1.-   Table 1.25: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is cyclopropyl, and    R⁸ is as defined above in Table 1.-   Table 1.26: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is ethoxy, and R⁸ is    as defined above in Table 1.-   Table 1.27: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is hydroxy, and R⁸    is as defined above in Table 1.-   Table 1.28: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is    2,2,2-trifluoroethyl, and R⁸ is as defined above in Table 1.-   Table 1.29: This table discloses 149 specific compounds of formula    (T-1) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is 2-hydroxyethyl,    and R⁸ is as defined above in Table 1.-   Table 2.1: This table discloses 26 specific compounds of the formula    (T-2):

wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹,R², R³, R⁴, R⁵ and R⁶ are hydrogen, R⁷ is methoxy and R¹² is as definedbelow in Table 2.

Each of Tables 2.2 to 2.5 (which follow Table 2.1) make available 26individual compounds of the formula (T-2) in which n, A¹, A², A³, A⁴,R¹, R², R³, R⁴, R⁵, R⁶ and R⁷ are as specifically defined in Tables 2.2to 2.5, which refer to Table 2 wherein R¹² is specifically defined.

TABLE 2 Compound no. R¹² 2.001 methyl 2.002 ethyl 2.003 propyl 2.004isopropyl 2.005 butyl 2.006 sec-butyl 2.007 tert-butyl 2.008 isobutyl2.009 allyl 2.010 but-3-ynyl 2.011 but-2-ynyl 2.012 prop-2-ynyl 2.0132-acetoxyethyl 2.014 2-hydroxyethyl 2.015 2-hydroxypropyl 2.0162-chloroethyl 2.017 2-fluoroethyl 2.018 3-chloropropyl 2.0193-fluoropropyl 2.020 4-chlorobutyl 2.021 2-cyanoethyl 2.0222-methoxyethyl 2.023 2-ethoxyethyl 2.024 2-methoxypropyl 2.025 phenyl2.026 phenylmethyl

-   Table 2.2: This table discloses 26 specific compounds of formula    (T-2) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is allyl, and R¹² is    as defined above in Table 2.-   Table 2.3: This table discloses 26 specific compounds of formula    (T-2) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is ethoxy, and R¹²    is as defined above in Table 2.-   Table 2.4: This table discloses 26 specific compounds of formula    (T-2) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is hydroxy, and R¹²    is as defined above in Table 2.-   Table 2.5: This table discloses 26 specific compounds of formula    (T-2) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is    2,2,2-trifluoroethyl, and R¹² is as defined above in Table 2.-   Table 3.1: This table discloses 100 specific compounds of the    formula (T-3):

wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹,R², R³, R⁴, R⁵, R⁶, and R¹⁵ are hydrogen, R⁷ is methoxy and R¹⁴ is asdefined below in Table 3.

Each of Tables 3.2 to 3.14 (which follow Table 3.1) make available 100individual compounds of the formula (T-3) in which n, A¹, A², A³, A⁴,R¹, R², R³, R⁴, R⁵, R⁶, R⁷ and R¹⁵ are as specifically defined in Tables3.2 to 3.14, which refer to Table 3 wherein R¹⁴ is specifically defined.

TABLE 3 Compound no. R¹⁴ 3.001 methyl 3.002 ethyl 3.003 propyl 3.004isopropyl 3.005 butyl 3.006 sec-butyl 3.007 tert-butyl 3.008 isobutyl3.009 pentyl 3.010 allyl 3.011 2-methylallyl 3.012 1,1-dimethylallyl3.013 prop-2-ynyl 3.014 2-acetoxyethyl 3.015 2-hydroxyethyl 3.0162-hydroxypropyl 3.017 3-hydroxypropyl 3.018 2,2-difluoroethyl 3.0192,2,2-trifluoroethyl 3.020 3,3,3-trifluoropropyl 3.0214,4,4-trifluorobutyl 3.022 but-3-ynyl 3.023 but-2-ynyl 3.0242-cyanoethyl 3.025 2-methoxyethyl 3.026 2-ethoxyethyl 3.0272-methoxypropyl 3.028 1-methoxy-4-piperidyl 3.029 oxetan-3-yl 3.030phenyl 3.031 pyrid-2-yl 3.032 pyrid-3-yl 3.033 pyrid-4-yl 3.034phenylmethyl 3.035 pyrid-2-ylmethyl 3.036 cyclopropyl 3.0371-cyanocyclopropyl 3.038 1-fluorocyclopropyl 3.039 1-methylcyclopropyl3.040 cyclobutyl 3.041 cyclopentyl 3.042 cyclohexyl 3.043cyclopropylmethyl 3.044 cyclobutylmethyl 3.045 cyclopentylmethyl 3.046cyclohexylmethyl 3.047 tetrahydrofuran-3-yl 3.048 tetrahydropyran-3-yl3.049 tetrahydropyran-4-yl 3.050 tetrahydrofuran-2-ylmethyl 3.051tetrahydrofuran-3-ylmethyl 3.052 tetrahydropyran-2-ylmethyl 3.053tetrahydropyran-3-ylmethyl 3.054 benzyl 3.055 furylmethyl 3.0561-methoxymethylcyclopropyl 3.057 1-ethoxycarbonylcyclopropyl 3.0581-hydroxycyclopropylmethyl 3.059 cyclopropyl-1-ethyl 3.0602,2-dimethylpropyl 3.061 cyano 3.062 1-methylprop-2-ynyl 3.0631-methylbut-2-ynyl 3.064 1,1-dimethylprop-2-ynyl 3.065 cyanomethyl 3.0662-cyanoethyl 3.067 3-cyanopropyl 3.068 1-methoxymethyl 3.0692-methoxyethyl 3.070 3-methoxypropyl 3.071 4-methoxybutyl 3.0721-methoxyethyl 3.073 1-(methoxymethyl)propyl 3.0742-methoxy-1,1-dimethylethyl 3.075 2-methoxyethoxymethyl 3.0761-acetoxymethyl 3.077 2-acetoxy-1,1-dimethylethyl 3.0782,2-diethoxyethyl 3.079 2,2-dimethoxyethyl 3.08 hydroxymethyl 3.0812-hydroxypropyl 3.082 2-hydroxy-1,1-dimethylethyl 3.0832-hydroxy-2-methylpropyl 3.084 trifluoromethyl 3.085 fluoromethyl 3.086difluoromethyl 3.087 2-fluoroethyl 3.088 2-chloroethyl 3.0893-chloropropyl 3.090 methoxy 3.091 ethoxy 3.092 propoxy 3.093 isopropoxy3.094 butoxy 3.095 sec-butoxy 3.096 isobutoxy 3.097 allyloxy 3.098prop-2-ynyloxy 3.099 ethoxycarbonylmethyl 3.100methylaminocarbonylmethyl

-   Table 3.2: This table discloses 100 specific compounds of formula    (T-3) wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R²,    R³, R⁴, R⁵, R⁶, and R¹⁵ are hydrogen, R⁷ is methoxy, R¹ is fluorine,    n is 1, and R¹⁴ is as defined above in Table 3.-   Table 3.3: This table discloses 100 specific compounds of formula    (T-3) wherein A¹ is N, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R²,    R³, R⁴, R⁵, R⁶, and R¹⁵ are hydrogen, R⁷ is methoxy, n is 1, and R¹⁴    is as defined above in Table 3.-   Table 3.4: This table discloses 100 specific compounds of formula    (T-3) wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹,    R², R⁴, R⁵, R⁶, and R¹⁵ are hydrogen, R⁷ is methoxy, R³ is fluorine,    n is 1, and R¹⁴ is as defined above in Table 3.-   Table 3.5: This table discloses 100 specific compounds of formula    (T-3) wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R³,    R⁴, R⁵, R⁶, and R¹⁵ are hydrogen, R⁷ is methoxy, R¹ and R² are    fluorine, n is 1, and R¹⁴ is as defined above in Table 3.-   Table 3.6: This table discloses 100 specific compounds of formula    (T-3) wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹,    R², R³, R⁴, R⁵, R⁶, and R¹⁵ are hydrogen, R⁷ is isopropyl, n is 2,    and R¹⁴ is as defined above in Table 3.-   Table 3.7: This table discloses 100 specific compounds of formula    (T-3) wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹,    R², R³, R⁴, R⁵, and R⁶, are hydrogen, R⁷ is methoxy, R¹⁵ is methyl,    n is 1, and R¹⁴ is as defined above in Table 3.-   Table 3.8: This table discloses 100 specific compounds of formula    (T-3) wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R²,    R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is methoxy, R¹ is fluorine, R¹⁵    is methyl, n is 1, and R¹⁴ is as defined above in Table 3.-   Table 3.9: This table discloses 100 specific compounds of formula    (T-3) wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹,    R², R⁴, R⁵, and R⁶ are hydrogen, R⁷ is methoxy, R³ is fluorine, R¹⁵    is methyl, n is 1, and R¹⁴ is as defined above in Table 3.-   Table 3.10: This table discloses 100 specific compounds of formula    (T-3) wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹,    R², R³, R⁴, R⁵, R⁶ and R¹⁵ are hydrogen, R⁷ is methyl, n is 1, and    R¹⁴ is as defined above in Table 3.-   Table 3.11: This table discloses 100 specific compounds of formula    (T-3) wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹,    R², R³, R⁴, R⁵, R⁶ and R¹⁵ are hydrogen, R⁷ is ethyl, n is 1, and    R¹⁴ is as defined above in Table 3.-   Table 3.12: This table discloses 100 specific compounds of formula    (T-3) wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹,    R², R³, R⁴, R⁵, R⁶ and R¹⁵ are hydrogen, R⁷ is isopropyl, n is 1,    and R¹⁴ is as defined above in Table 3.-   Table 3.13: This table discloses 100 specific compounds of formula    (T-3) wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹,    R², R³, R⁴, R⁵, R⁶ and R¹⁵ are hydrogen, R⁷ is cyclopropyl, n is 1,    and R¹⁴ is as defined above in Table 3.-   Table 3.14: This table discloses 100 specific compounds of formula    (T-3) wherein A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹,    R², R³, R⁴, R⁵, R⁶ and R¹⁵ are hydrogen, R⁷ is hydroxy, n is 1, and    R¹⁴ is as defined above in Table 3.-   Table 4.1: This table discloses 4 specific compounds of the formula    (T-4):

wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴ and R¹,R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is methoxy, and R¹⁴—N—R¹⁵ is asdefined below in the Table 4.

Each of Tables 4.2 to 4.4 (which follow Table 4.1) make available 4individual compounds of the formula (T-4) in which n, A¹, A², A³, A⁴,R¹, R², R³, R⁴, R⁵, R⁶, and R⁷ are as specifically defined in Tables 4.2to 4.4, which refer to Table 4 wherein R¹⁴—N—R¹⁵ is specificallydefined.

TABLE 4 Compound no. R¹⁴—N—R¹⁵ 4.001 pyrolidine 4.002 piperidine 4.003morpholine 4.004 isooxazolidine

-   Table 4.2: This table discloses 4 specific compounds of formula    (T-4) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶ are hydrogen, R⁷ is methyl, and    R¹⁴—N—R¹⁵ is as defined above in Table 4.-   Table 4.3: This table discloses 4 specific compounds of formula    (T-4) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, and R⁶, are hydrogen, R⁷ is ethyl and    R¹⁴—N—R¹⁵ is as defined above in Table 4.-   Table 4.4: This table discloses 4 specific compounds of formula    (T-4) wherein n is 1, A¹ is C—R¹, A² is C—R², A³ is C—R³, A⁴ is C—R⁴    and R¹, R², R³, R⁴, R⁵, R⁶ are hydrogen, R⁷ is isopropyl, and    R¹⁴—N—R¹⁵ is as defined above in Table 4.

EXAMPLES

The Examples which follow serve to illustrate the invention. Thecompounds of the invention can be distinguished from known compounds byvirtue of greater efficacy at low application rates, which can beverified by the person skilled in the art using the experimentalprocedures outlined in the Examples, using lower application rates ifnecessary, for example 50 ppm, 12.5 ppm, δppm, 3 ppm, 1.5 ppm or 0.2ppm.

Compounds of Formula (I) (including those according to the invention)may possess any number of benefits including, inter alia, advantageouslevels of biological activity for protecting plants against diseasesthat are caused by fungi or superior properties for use as agrochemicalactive ingredients (for example, greater biological activity, anadvantageous spectrum of activity, an increased safety profile(including improved crop tolerance), improved physico-chemicalproperties, or increased biodegradability).

Throughout this description, temperatures are given in degrees Celsius(° C.) and “mp.” means melting point. LC/MS means Liquid ChromatographyMass Spectrometry and the description of the apparatus and the method(Methods A and B) is as follows:

The Description of the LC/MS Apparatus and the Method A is:

-   SQ Detector 2 from Waters-   Ionisation method: Electrospray-   Polarity: positive and negative ions-   Capillary (kV) 3.0, Cone (V) 30.00, Extractor (V) 2.00, Source    Temperature (° C.) 150, Desolvation-   Temperature (° C.) 350, Cone Gas Flow (L/Hr) 0, Desolvation Gas Flow    (L/Hr) 650-   Mass range: 100 to 900 Da-   DAD Wavelength range (nm): 210 to 500-   Method Waters ACQUITY UPLC with the following HPLC gradient    conditions:-   (Solvent A: Water/Methanol 20:1+0.05% formic acid and Solvent B:    acetonitrile+0.05% formic acid)

Time (minutes) A (%) B (%) Flow rate (ml/min) 0 100 0 0.85 1.2 0 1000.85 1.5 0 100 0.85

-   Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm;    Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron;    Temperature: 60° C.    The description of the LC/MS apparatus and the method B is:-   SQ Detector 2 from Waters-   Ionisation method: Electrospray-   Polarity: positive ions-   Capillary (kV) 3.5, Cone (V) 30.00, Extractor (V) 3.00, Source    Temperature (° C.) 150, Desolvation-   Temperature (° C.) 400, Cone Gas Flow (L/Hr) 60, Desolvation Gas    Flow (L/Hr) 700-   Mass range: 140 to 800 Da-   DAD Wavelength range (nm): 210 to 400-   Method Waters ACQUITY UPLC with the following HPLC gradient    conditions-   (Solvent A: Water/Methanol 9:1+0.1% formic acid and Solvent B:    acetonitrile+0.1% formic acid)

Time (minutes) A (%) B (%) Flow rate (ml/min) 0 100 0 0.75 2.5 0 1000.75 2.8 0 100 0.75 3.0 100 0 0.75

-   Type of column: Waters ACQUITY UPLC HSS T3; Column length: 30 mm;    Internal diameter of column: 2.1 mm; Particle Size: 1.8 micron;    Temperature: 60° C.

Where necessary, enantiomerically pure final compounds may be obtainedfrom racemic materials as appropriate via standard physical separationtechniques, such as reverse phase chiral chromatography, or throughstereoselective synthetic techniques, eg, by using chiral startingmaterials.

FORMULATION EXAMPLES

Wettable Powders

a) b) c) active ingredient [compound of formula (I)] 25%  50%  75% sodium lignosulfonate 5% 5% — sodium lauryl sulfate 3% — 5% sodiumdiisobutylnaphthalenesulfonate — 6% 10%  phenol polyethylene glycolether — 2% — (7-8 mol of ethylene oxide) highly dispersed silicic acid5% 10%  10%  Kaolin 62%  27%  —

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording wettablepowders that can be diluted with water to give suspensions of thedesired concentration.

Powders for Dry Seed Treatment

a) b) c) active ingredient [compound of formula (I)] 25% 50% 75% lightmineral oil  5%  5%  5% highly dispersed silicic acid  5%  5% — Kaolin65% 40% — Talcum — 20%

The active ingredient is thoroughly mixed with the adjuvants and themixture is thoroughly ground in a suitable mill, affording powders thatcan be used directly for seed treatment.

Emulsifiable Concentrate

active ingredient [compound of formula (I)] 10% octylphenol polyethyleneglycol ether 3% (4-5 mol of ethylene oxide) calciumdodecylbenzenesulfonate 3% castor oil polyglycol ether (35 mol ofethylene oxide) 4% Cyclohexanone 30% xylene mixture 50%

Emulsions of any required dilution, which can be used in plantprotection, can be obtained from this concentrate by dilution withwater.

Dusts

a) b) c) Active ingredient [compound of formula (I)]  5%  6%  4% Talcum95% — — Kaolin — 94% — mineral filler — — 96%

Ready-for-use dusts are obtained by mixing the active ingredient withthe carrier and grinding the mixture in a suitable mill. Such powderscan also be used for dry dressings for seed.

Extruder Granules

Active ingredient [compound of formula (I)] 15% sodium lignosulfonate 2%Carboxymethylcellulose 1% Kaolin 82%

The active ingredient is mixed and ground with the adjuvants, and themixture is moistened with water. The mixture is extruded and then driedin a stream of air.

Coated Granules

Active ingredient [compound of formula (I)] 8% polyethylene glycol (mol.wt. 200) 3% Kaolin 89%

The finely ground active ingredient is uniformly applied, in a mixer, tothe kaolin moistened with polyethylene glycol. Non-dusty coated granulesare obtained in this manner.

Suspension Concentrate

active ingredient [compound of formula (I)] 40% propylene glycol 10%nonylphenol polyethylene glycol ether (15 mol of ethylene oxide) 6%Sodium lignosulfonate 10% Carboxymethylcellulose 1% silicone oil (in theform of a 75% emulsion in water) 1% Water 32%

-   -   The finely ground active ingredient is intimately mixed with the        adjuvants, giving a suspension concentrate from which        suspensions of any desired dilution can be obtained by dilution        with water. Using such dilutions, living plants as well as plant        propagation material can be treated and protected against        infestation by microorganisms, by spraying, pouring or        immersion.        Flowable Concentrate for Seed Treatment

active ingredient [compound of formula (I)] 40%  propylene glycol 5%copolymer butanol PO/EO 2% tristyrenephenole with 10-20 moles EO 2%1,2-benzisothiazolin-3-one (in the form 0.5%   of a 20% solution inwater) monoazo-pigment calcium salt 5% Silicone oil (in the form of a75% emulsion in water) 0.2%   Water 45.3%  

The finely ground active ingredient is intimately mixed with theadjuvants, giving a suspension concentrate from which suspensions of anydesired dilution can be obtained by dilution with water. Using suchdilutions, living plants as well as plant propagation material can betreated and protected against infestation by microorganisms, byspraying, pouring or immersion.

Slow-Release Capsule Suspension

28 parts of a combination of the compound of formula I are mixed with 2parts of an aromatic solvent and 7 parts of toluenediisocyanate/polymethylene-polyphenylisocyanate-mixture (8:1). Thismixture is emulsified in a mixture of 1.2 parts of polyvinylalcohol,0.05 parts of a defoamer and 51.6 parts of water until the desiredparticle size is achieved. To this emulsion a mixture of 2.8 parts1,6-diaminohexane in 5.3 parts of water is added. The mixture isagitated until the polymerization reaction is completed.

The obtained capsule suspension is stabilized by adding 0.25 parts of athickener and 3 parts of a dispersing agent. The capsule suspensionformulation contains 28% of the active ingredients. The medium capsulediameter is 8-15 microns.

The resulting formulation is applied to seeds as an aqueous suspensionin an apparatus suitable for that purpose.

List of Abbreviations:

-   AIBN=azobisisobutyronitrile-   BOP-Cl=phosphoric acid bis(2-oxooxazolidide) chloride-   CDl=carbonyl diimidazole-   DCE=1,2-dichloroethane-   DCM=dichloromethane-   DIBAL-H=diisobutylaluminium hydride-   DIPEA=N,N-diisopropylethylamine-   DMA=dimethylacetamide-   DMF=dimethylformamide-   EdCl=3-(ethyliminomethyleneamino)-N,N-dimethylpropan-1-amine-   EtOAc=ethyl acetate-   EtOH=ethyl alcohol-   HCl=hydrochloric acid-   HOAt=1-hydroxy-7-azabenzotriazole-   HATU=1-[bis(dimethylamino)methylene]-1H-1,2,3-triazolo[4,5-b]pyridinium    3-oxid-hexafluorophosphate-   min=minutes-   mp=melting point-   MeOH=methyl alcohol-   NaOH=sodium hydroxide-   NBS=N-bromosuccinimide-   TFAA=trifluoroacetic acid anhydride-   THF=tetrahydrofuran

PREPARATION EXAMPLES

Using the synthetic techniques described both above and below, compoundsof formula (I) may be prepared accordingly.

Example 1

This example illustrates the preparation ofN-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-acetamide(Compound 1.1 of Table T1 below).

Step 1: Preparation of4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoyl chloride

4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoic acid (4.00 g, 15.0mmol) was suspended in dichloromethane (90 mL) DMF (0.01 mL, 0.150 mmol)was added followed by oxalyl chloride (1.46 mL, 16.5 mmol). The mixturewas heated at reflux for 2 hours. The mixture was evaporated underreduced pressure to afford 4.15 g of4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoyl chloride as a yellowsolid.

Step 2: Preparation ofN-methoxy-N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide

A solution of 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzoylchloride from Step 1 (4.15 g, 14.6 mmol) in dichloromethane (20 mL) wasadded drop wise at room temperature to a stirred solution ofN-methoxymethanamine (1.10 g, 17.5 mmol) and triethylamine (3.10 ml,21.8 mmol) in dichloromethane (80 mL). The mixture was stirred at roomtemperature for 18 hours. The reaction mixture was poured into waterextracted twice with dichloromethane. The combined organic layers werewashed with brine, dried over sodium sulfate, and filtered. The solventwas removed under reduced pressure and the resultant crude residue wassubjected to flash chromatography over silica gel (heptane: EtOAc eluentgradient 9:1 to 65:35) to afford 4.12 g ofN-methoxy-N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamideas a solid. LC/MS (Method A) retention time=0.97 minutes, 302 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 8.18 (d, 2H), 7.84 (d, 2H), 3.56 (s, 3H),3.40 (s, 3H).

Step 3: Preparation of4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde

In a 75-mL multi neck flask equipped with stirrer, thermometer at −78°C. under argon, DIBAL-H, 1.0 M in toluene (16 mL, 16.0 mmol) was addeddrop-wise to a solution ofN-methoxy-N-methyl-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzamide(4.10 g, 13.3 mmol) in 2-methyltetrahydrofuran (90 mL). The mixture wasstirred two hours at −78° C. and for one hour temperature was letincrease to 0° C. Complete conversion observed by LC-MS. The mixture wasquenched by drop wise addition of sat. ammonium chloride solution.Precipitation of a white solid occurred. 4 M HCl was added until fullsolubilisation. The mixture was extracted thrice with ethyl acetate.Combined organics were dried over magnesium sulfate and evaporated toafford the crude as beige solid. The crude was subject to flashchromatography over silicagel (heptane: EtOAc eluent gradient 99:1 to90:10) to afford 2.93 g of4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde as a whitesolid mp: 40-50° C.

¹H NMR (400 MHz, CDCl₃) δppm: 10.12 (s, 1H), 8.31 (d, 2H), 8.05 (d, 2H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.29 (s).

Step 4: Preparation ofN-methoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanimine

A solution of 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde(0.30 g, 1.1 mmol) in methanol (11 mL) was treated at room temperaturewith pyridine (0.15 mL, 1.9 mmol) followed by addition ofO-methylhydroxylamine hydrochloride (0.15 g, 1.8 mmol). The mixture wasstirred at room temperature over the weekend, poured on water, acidifiedwith 1 M HCl and extracted trice with ethyl acetate. Combined organicswere washed with water, dried over magnesium sulfate and evaporated toafford a resin. The crude was subject to flash chromatography oversilicagel (heptane: EtOAc eluent gradient 100:0 to 95:5) to afford thetitle compound as a white solid mp: 55-65° C.

¹H NMR (400 MHz, CDCl₃) δppm: 8.14 (s, 1H), 8.11 (d, 2H), 7.73 (d, 2H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.40 (s).

Step 5: Preparation ofN-methoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine

A solution ofN-methoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanimine(0.81 g, 2.89 mmol) in acetic acid (11 mL) was treated at 15° C. withsodium cyano borohydride (0.4 g, 6.1 mmol). The mixture was stirred at22° C. for 18 hours until complete consumption of starting material wasobserved. The reaction mixture was carefully poured in 0.1 M NaOHsolution. By addition of 1 M NaOH pH was adjusted to 12-13. The mixturewas extracted four times with TBME. Combined organics were washed twicewith water and once with brine then dried over magnesium sulfate andconcentrated under reduced. The resultant green oil was purified byflash chromatography over silica gel (heptane: EtOAc eluent gradient99:1 to 70:30) to give 0.60 g of the title compound as an oil.

¹H NMR (400 MHz, CDCl₃) δppm: 8.09 (d, 2H), 7.53 (d, 2H), 5.33 (S_(br),1H), 4.12 (s, 2H), 3.50 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.32 (s).

Step 6: Preparation ofN-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-acetamide

To a stirred solution of acetic acid (0.03 g, 0.49 mmol), EDCl (0.15 g,0.76 mmol), HOAt (0.03 g, 0.19 mmol) and triethylamine (0.16 mL, 1.14mmol) in dry dichloromethane (2.9 mL) under an atmosphere of nitrogen atroom temperature was addedN-methoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine(0.11 g, 0.38 mmol). The reaction mixture was stirred at roomtemperature for 18 hours and then 1 M HCl and dichloromethane wereadded. The resultant mixture was shaken and the layers were separated.The aqueous layer was extracted trice with dichloromethane and thecombined organic layers were washed with brine, dried over sodiumsulfate, filtered and evaporated to dryness. The crude oil was purifiedby flash chromatography over silica gel (heptane: EtOAc eluent gradient99:1 to 80:20) to give 0.08 g of the title compound as a clear oil.

LC/MS (Method A) retention time=0.98 minutes, 316.3 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 8.09 (d, 2H), 7.47 (d, 2H), 4.86 (s, 2H),3.68 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.34 (s).

Example 2

This example illustrates the preparation of Intermediate3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

Step 1: Preparation of N′-hydroxy-4-methyl-benzamidine

To a stirred suspension of 4-methylbenzonitrile (35 g, 0.29 mol) inethanol (220 mL) and water (440 mL) was added at room temperaturehydroxylamine hydrochloride (41.1 g, 0.58 mol), potassium carbonate(65.4 g, 0.47 mol) and 8-hydroxyquinoline (0.22 g, 1.5 mmol). Thereaction mixture was heated at 80° C. for 4 hours. The mixture wascooled to room temperature and diluted with 2N HCl until pH 8. Ethanolwas evaporated under reduced pressure. The mixture was filtered, washedwith water and dried under vacuum to afford 39.1 g of the titlecompound. LC/MS (Method A) retention time=0.23 minutes, 151.0 (M+H).

Step 2: Preparation of 3-(p-tolyl)-5-(trifluoromethyl)-1,2,4-oxadiazole

To a stirred solution of N′-hydroxy-4-methyl-benzamidine (38.7 g, 0.25mol) in 2-methyltetrahydrofuran (750 mL) was added TFAA at 0° C. Thereaction mixture was stirred at 15° C. for two hours and diluted withwater. The organic layer was separated, washed successively with sodiumbicarbonate solution, ammonium chloride solution and water, dried oversodium sulfate, filtered and evaporated to dryness. The crude wassubject to flash chromatography over silica gel (750 g prepacked column)with heptane/EtOAc 99:1 to 90:10 to afford 54.1 g of the title compoundas clear oil, which solidified after storage.

LC/MS (Method A) retention time=1.15 minutes, mass not detected.

¹H NMR (400 MHz, CDCl₃) δppm: 8.00 (d, 2H), 7.32 (d, 2H), 2.45 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.41 (s).

Step 3a: Preparation of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

A stirred mixture of 3-(p-tolyl)-5-(trifluoromethyl)-1,2,4-oxadiazole(56.0 g, 0.24 mol) and NBS (45.4 g, 0.25 mol) in tetrachloromethane (480mL) under argon was heated to 70° C. AIBN (4.03 g, 24 mmol) was addedand the reaction mixture was stirred at 65° C. for 18 hours. The mixturewas cooled to room temperature and diluted with dichloromethane andwater. Layers were separated. The organic layer was washed with sodiumbicarbonate solution, dried over sodium sulfate, filtered and evaporatedto dryness. The crude was subject to flash chromatography over silicagel(750 g pre packed column) with cyclohehane/EtOAc 100:0 to 95:5 to afford44.7 g of the title compound as a white solid mp: 58-63° C.

¹H NMR (400 MHz, CDCl₃) δppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.32 (s).

3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole wasisolated as by-product as white solid mp: 61-66° C.

¹H NMR (400 MHz, CDCl₃) δppm: 8.15 (d, 2H), 7.73 (d, 2H), 6.68 (s, 1H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.34 (s).

Step 3b: Preparation of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole from3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

To a 1:9 ratio mixture of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole and3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (10.2g) in acetonitrile (95 mL), water (1.9 mL) and DIPEA (6.20 ml, 35.7mmol) was added diethylphosphite (4.7 ml, 35.7 mmol) at 5° C. Themixture was stirred at 5-10° C. for two hours, water and 1 M HCl wasadded and acetonitrile was evaporated under reduced pressure. The whiteslurry was extracted thrice with dichloromethane. The combined organiclayers were dried over sodium sulfate, and filtered. The solvent wasremoved under reduced pressure and the resultant crude was subject toflash chromatography over silicagel (40 g prepacked column) withcyclohexane/EtOAc 99:1 to 9:1 to afford 7.10 g of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole.

¹H NMR (400 MHz, CDCl₃) δppm: 8.11 (d, 2H), 7.55 (d, 2H), 4.53 (s, 2H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.32 (s).

Example 3

This example illustrates the preparation of intermediateN-propoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine

A solution of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (1.30 g,4.06 mmol) in dichloromethane (10 mL) was added drop wise at roomtemperature to a stirred solution of O-propylhydroxylamine hydrochloride(3.74 g, 32.5 mmol) and DIEA (6.40 ml, 36.6 mmol) in dichloromethane (6mL). The mixture was stirred at room temperature for 24 hours. Thereaction mixture was poured onto water and the layers were separated.The aqueous layer was extracted trice with dichloromethane. The combinedorganic layers were washed with brine, dried over sodium sulfate, andfiltered. The solvent was removed under reduced pressure and theresultant crude was purified by flash chromatography over silica gel(cyclohexane: EtOAc eluent gradient 1:0 to 1:1) to give 0.92 g of thetitle compound as a clear oil. LC/MS (Method A) retention time=1.12minutes, 302 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 8.09 (d, 2H), 7.02 (d, 2H), 5.70 (s_(br),1H), 4.11 (s, 2H), 3.59 (m, 2H), 1.52 (m, 2H), 0.86 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.33 (s).

Example 4

This example illustrates the preparation of intermediateN-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]ethanamine.

A solution of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (1.50 g,4.69 mmol) in dichloromethane (9.4 mL) was added drop-wise at roomtemperature to a stirred solution of ethylamine 2 M in MeOH (12 mL, 24.0mmol). The mixture was stirred at room temperature for 24 hours. Thereaction mixture was poured into water and the layers were separated.The aqueous layer was extracted trice with dichloromethane. The combinedorganic layers were washed with brine, dried over sodium sulfate andfiltered. The solvent was removed under reduced pressure and theresultant crude was purified by flash chromatography over silica gel(cyclohexane: EtOAc eluent gradient 1:0 to 1:1) to give 0.92 g of thetitle compound as a white solid mp: 102-112° C., LC/MS (Method A)retention time=0.66 minutes, 272 (M+H).

¹H NMR (400 MHz, DMSO) δppm: 8.01 (d, 2H), 7.57 (d, 2H), 3.86 (q, 2H),3.29 (s_(br), 1H), 2.53 (q, 2H), 1.05 (t, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −64.77 (s).

Example 5

This example illustrates the preparation of the intermediateN-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]ethanamine.

A solution of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (1.50 g,4.69 mmol) in dichloromethane (9.4 mL) was added drop wise at roomtemperature to a stirred solution of sec-butylamine (2.4 mL, 23.4 mmol)in dichloromethane (5 mL). The mixture was stirred at room temperaturefor 24 hours. The reaction mixture was poured into water and extractedtrice with dichloromethane. The combined organic layers were washed withbrine, dried over sodium sulfate, and filtered. The solvent was removedunder reduced pressure and the resultant crude residue was purified byflash chromatography over silica gel (cyclohexane: EtOAc eluent gradient1:0 to 1:1) to give 1.18 g of the title compound as a clear oil, LC/MS(Method A) retention time=0.71 minutes, 300 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 8.06 (d, 2H), 7.49 (d, 2H), 3.86 (q, 2H),2.62 (m, 1H), 1.53 (m, 1H), 1.49 (m, 1H), 1.09 (d, 3H), 0.91 (m, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.39 (s).

Example 6

This example illustrates the preparation of the intermediateN-methoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanamine.

Step 1: Preparation of4-[(E)-N-methoxy-C-methyl-carbonimidoyl]benzonitrile

A solution of 4-acetyl benzonitrile (5.0 g, 33.8 mmol) in EtOH (270 mL)was treated at room temperature with 0-methylhydroxylamine hydrochloride(4.32 g, 50.6 mmol). The mixture was stirred at room temperature for 70hours, poured on water and extracted thrice with dichloromethane.Combined organics were washed with water, dried over magnesium sulfateand evaporated to afford 5.95 g of the title compound as clear oil. Nofurther purification was required. LC/MS (Method A) retention time=0.93minutes, 175 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 7.78 (d, 2H), 7.65 (d, 2H), 4.03 (s, 3H),2.22 (s, 3H).

Step 2: Preparation ofN′-hydroxy-4-[(E)-N-methoxy-C-methyl-carbonimidoyl]benzamidine

To a stirred suspension of4-[(E)-N-methoxy-C-methyl-carbonimidoyl]benzonitrile (5.95 g, 33.5 mmol)in ethanol (50 mL) and water (100 mL) was added at room temperaturehydroxylamine hydrochloride (4.7 g, 66.9 mmol), potassium carbonate(7.48 g, 53.6 mmol) and 8-hydroxyquinoline (0.025 g, 0.17 mmol). Thereaction mixture was heated at 80° C. for 3 hours. The mixture wascooled to room temperature and 1 M HCl was added until pH 8-9. Ethanolwas removed under reduced pressure at 50° C. The mixture was stirred 30minutes at 5° C., filtered, washed with water and dried under vacuum toafford 6.6 g of the title compound as a white solid mp: 134-139° C.,LC/MS (Method A) retention time=0.43 minutes, 208 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 8.23 (s_(br), 1H), 7.69 (d, 2H), 7.62 (d,2H), 4.88 (s_(br), 2H), 4.00 (s, 3H), 2.23 (s, 3H).

Step 3: Preparation ofN-methoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanimine

To a stirred solution ofN′-hydroxy-4-[(E)-N-methoxy-C-methyl-carbonimidoyl]benzamidine (6.46 g,31.2 mmol) in 2-methyltetrahydrofuran (93 mL) was added TFAA (6.24 mL,43.7 mmol) at 15° C. The reaction mixture was stirred at 15° C. for twohours and diluted with water. The organic layer was separated and washedsuccessively with sodium bicarbonate solution, ammonium chloridesolution and water, dried over sodium sulfate, filtered and evaporatedto dryness to afford 8.9 g of the title compound as beige solid mp:56-61° C., LC/MS (Method A) retention time=1.19 minutes, 286 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 8.13 (d, 2H), 7.81 (d, 2H), 4.03 (s, 3H),2.25 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.34 (s).

Step 4: Preparation ofN-methoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanamine

A solution ofN-methoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethanimine(8.9 g, 29.6 mmol) in acetic acid (119 mL) was treated at 15° C. portionwise with sodium cyano borohydride (4.12 g, 62.3 mmol). The mixture wasstirred at 23° C. for 18 hours. Partial consumption of starting materialwas observed. Additional cyano borohydride (4.12 g, 62.3 mmol) was addedportion wise. The reaction mixture was carefully poured in 0.1 M sodiumhydroxide solution. By addition of 4 M NaOH pH was adjusted to 9-12. Themixture was extracted four times with TBME. Combined organics werewashed twice with water and once with brine then dried over magnesiumsulfate and concentrated under reduced. The resultant green oil waspurified by flash chromatography over silica gel (heptane: EtOAc eluentgradient 99:1 to 70:30) to give 5.0 g of the title compound as an oil.LC/MS retention time=1.05 minutes, 288 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 8.10 (d, 2H), 7.51 (d, 2H), 5.65 (S_(br),1H), 4.22 (q, 1H), 3.47 (s, 3H), 1.38 (d, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.37 (s).

Example 7

This example illustrates the preparation of the1-[cyano-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3-methoxy-1,3-dimethyl-urea(Compound 3.31 of Table T3)

Step 1: Preparation of2-(methylamino)-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetonitrile

To a stirred solution of4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]benzaldehyde (2.5 g, 10.3mmol) in THF (16 mL) was added at room temperature methylamine (0.38 g,12.4 mmol). After 10 minutes water (51.6 ml) and acetone cyanohydrin(0.8 g, 10.3 mmol) was added. The mixture was stirred overnight, pouredon water and extracted twice with ethyl acetate. The organic layer waswashed successively with brine, dried over sodium sulfate, filtered andevaporated to dryness. The crude was subject to flash chromatographyover silica gel with cyclohexane/t-butylmethylether 9:1 to afford 2.1 gof the title compound as white solid.

¹H NMR (400 MHz, CDCl₃) δppm: 8.17 (d, 2H), 7.72 (d, 2H), 4.87 (s, 1H),2.61 (s, 3H), 1.62 (S_(br), 1H).

Step 2: Preparation of1-[cyano-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3-methoxy-1,3-dimethyl-urea

To a stirred solution of2-(methylamino)-2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]acetonitrile(0.17 g, 0.60 mmol) in dichloromethane (5 mL) under an atmosphere ofnitrogen was added at 0° C. triethylamine (0.17 mL, 1.20 mmol),N,N-dimethylpyridin-4-amine (0.07 g, 0.60 mmol) followed byN,N-dimethylcarbamoyl chloride (0.09 g, 0.72 mmol). The reaction mixturewas stirred for 18 hours at room temperature, poured on HCl 1 M solutionand extracted with dichloromethane. The combined organic layers werewashed with 1 M NaOH, brine, dried over sodium sulfate, and filtered.The solvent was removed under reduced pressure and the resultant cruderesidue was subjected to flash chromatography over silica gel(cyclohexane: EtOAc eluent gradient 7:1 to 5:1) to afford 0.085 g of1-[cyano-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-3-methoxy-1,3-dimethyl-ureaas a white solid mp: 106-107° C.

¹H NMR (400 MHz, CDCl₃) δppm: 8.20 (d, 2H), 7.67 (d, 2H), 6.57 (s, 1H),3.67 (s, 3H), 3.11 (s, 3H), 2.86 (s, 3H).

Example 8 Preparation ofN-(oxetan-3-yl)-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide(Compound 1.604 of Table T1) Step 1: Preparation ofN-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]oxetan-3-amine

To a stirred solution of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (2.0 g,6.25 mmol) in dichloromethane (13 mL) was added drop wise at roomtemperature N-ethyl-N-isopropyl-propan-2-amine (1.1 mL) followed by theaddition of oxetan-3-amine (3.5 g, 50 mmol). The mixture was stirred atroom temperature for 24 hours. The reaction mixture was poured intowater and extracted trice with dichloromethane. The combined organiclayers were washed with brine, dried over sodium sulfate, and filtered.The solvent was removed under reduced pressure and the resultant cruderesidue was purified by flash chromatography over silica gel(cyclohexane: EtOAc eluent gradient 1:0 to 0:1) to give the titlecompound as a clear oil.

¹H NMR (400 MHz, CDCl₃) δppm: 8.08 (d, 2H), 7.48 (d, 2H), 4.80 (t, 2H),4.44 (t, 2H), 4.04 (m, 1H), 3.83 (s, 2H), 2.01 (s, 1H).

Step 2: Preparation ofN-(oxetan-3-yl)-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]propanamide

To a stirred suspension ofN-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]oxetan-3-amine(0.10 g, 0.33 mmol) in dichloromethane (6 mL) under an atmosphere ofnitrogen was added triethylamine (0.09 mL, 0.66 mmol) at 0° C. followedby propanoyl chloride (0.03 mL, 0.35 mmol). The reaction mixture wasevaporated under reduced pressure and the resultant crude residue wassubjected to flash chromatography over silica gel (heptane: EtOAc eluentgradient 9:1 to 1:9) to afford the desired product as a white solid mp:88.8°-93.5° C.

Example 8N-(2,2,2-trifluoroethyl)-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]tetrahydrofuran-2-carboxamide(Compound 1.587 of Table T1)

Step 1: Preparation of2,2,2-trifluoro-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]ethanamine

To a stirred solution of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (1.5 g,4.69 mmol) in dichloromethane (10 mL) was added drop wise at roomtemperature N-ethyl-N-isopropyl-propan-2-amine (0.82 mL, 4.69 mmol)followed by the addition of 2,2,2-trifluoroethanamine (2.94 mL, 37.5mmol). The mixture was stirred at room temperature for 24 hours. Thereaction mixture was poured into water and extracted trice withdichloromethane. The combined organic layers were dried over sodiumsulfate, and filtered. The solvent was removed under reduced pressureand the resultant crude residue was purified by flash chromatographyover silica gel (cyclohexane: EtOAc eluent gradient 1:0 to 0:1) to givethe title compound as a clear oil.

¹H NMR (400 MHz, CDCl₃) δppm: 8.09 (d, 2H), 7.51 (d, 2H), 4.00 (s, 2H),3.22 (q, 2H), 1.71 (s, 1H).

Step 2: Preparation ofN-(2,2,2-trifluoroethyl)-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]tetrahydrofuran-2-carboxamide

To a stirred suspension of2,2,2-trifluoro-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]ethanamine(0.09 g, 0.27 mmol) in dichloromethane (6 mL) under an atmosphere ofnitrogen was added triethylamine (0.08 mL, 0.55 mmol) at 0° C. followedby tetrahydrofuran-2-carbonyl chloride (0.04 g, 0.29 mmol). The reactionmixture was evaporated under reduced pressure and the resultant cruderesidue was subjected to combiflash chromatography over 12 g pre packedsilica gel (heptane: EtOAc eluent gradient 9:1 to 1:9) to afford thedesired product as a clear yellowish oil. LC/MS (Method A) retentiontime=1.14 minutes, 424.3 (M+H).

Example 9

This example illustrates the preparationN-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-N,2-dimethoxy-propanamide (Compound 1.783 of Table T1)

Step 1: Preparation of 2-fluoro-N′-hydroxy-4-methyl-benzamidine

To a suspension of 2-fluoro-4-methylbenzonitrile (5 g, 37.0 mmol) inethanol (125 mL) at 25° C. was added hydroxylamine hydrochloride (7.7 g,111 mmol). The reaction mixture was heated at 80° C. for 2 h. Aftercooling to room temperature the volatiles were removed under reducedpressure thus affording a white solid that was used in the next stepwithout any purification. LC/MS (Method A) retention time=1.14 minutes,169.2 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 7.96 (t, 1H), 7.11 (m, 2H), 2.45 (s, 3H).

Step 2: Preparation of3-(2-fluoro-4-methyl-phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole

To a solution of 2-fluoro-N′-hydroxy-4-methyl-benzamidine (37 mmol) intetrahydrofuran (122 mL) cooled via an ice bath was added TFAA (7.71 mL,55.5 mmol). The reaction mixture was stirred at 25° C. overnight andthen diluted with water. The organic layer was separated, washedsuccessively with sodium bicarbonate solution, ammonium chloridesolution, and water then dried over sodium sulfate, filtered andevaporated to dryness. The crude product was subjected to flashchromatography over silica gel with cyclohexane/EtOAc 99:1 to 1:1 toafford the title compound (6.6 g, 72% yield) as an amorphous whitesolid. LC/MS (Method A) retention time=1.14 minutes, 247 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 8.00 (d, 1H), 7.32 (d, 2H), 2.45 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.3 (s), 108.1 (s).

Step 3a: Preparation of3-[4-(bromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

A stirred mixture of3-(2-fluoro-4-methyl-phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole (4.2g, 17.1 mmol) and NBS (3.11 g, 17.1 mmol) in tetrachloromethane (34.3mL) under argon was heated to 70° C. AIBN (0.29 g, 1.71 mmol) was addedand the reaction mixture stirred at 65° C. for 18 h. The mixture wascooled to 25° C. then diluted with dichloromethane and water after whichthe layers were separated. The succinimide by-product was filtrated off,and the solvent was removed under reduced pressure to afford a browngum. This crude residue was subjected to flash chromatography oversilica gel (with cyclohexane/EtOAc 100:0 to 4:1 to afford the titlecompound as a white solid (1.7 g, 31% yield. LC/MS (Method A) retentiontime=1.13 minutes, (M+H) not detected.

¹H NMR (400 MHz, CDCl₃) δppm: 8.09 (t, 1H), 7.34 (m, 2H), 4.49 (s, 2H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.18 (s), -106.2 (s).

3-[4-(dibromomethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole wasisolated as by-product in the form of a beige solid (4.0 g, 58% yield)LC/MS (Method A) retention time=1.20 minutes, (M+H) not detected.

¹H NMR (400 MHz, CDCl₃) δppm: 8.14 (d, 1H), 7.52 (dd, 2H), 6.63 (s, 1H).

Step 3b: Preparation of3-[4-(bromomethyl)-2-fluoro-phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazolefrom33-[4-(dibromomethyl)-2-fluoro-phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

To a 1:20 ratio mixture of3-[4-(bromomethyl)-2-fluoro-phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazoleand3-[4-(dibromomethyl)-2-fluoro-phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole(4.0 g, 9.9 mmol) in acetonitrile (37 mL), water (0.8 mL) and DIPEA(2.59 mL, 14.8 mmol) at 5° C. was added diethylphosphite (2.0 mL, 14.8mmol). The mixture was stirred at 5-10° C. for 2 h, water and 1 M HClwere added, and volatiles were removed under reduced pressure. The whiteslurry was extracted three times with dichloromethane and the combinedorganic layers were dried over sodium sulfate and filtered. The solventwas removed under reduced pressure and the resultant light orangecolored crude residue was subjected to flash chromatography over silicagel with cyclohexane/EtOAc 99:1 to 1:1 to afford3-[4-(bromomethyl)-2-fluoro-phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole(2.2 g, 68% yield). LC/MS (Method A) retention time=1.13 minutes, (M+H)not detected.

¹H NMR (400 MHz, CDCl₃) δppm: 8.09 (t, 1H), 7.34 (m, 2H), 4.49 (s, 2H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.18 (s), −106.2 (s).

Step 4: Preparation of1-[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-N-methoxy-methanamine

A solution of 0-methylhydroxylamine hydrochloride (4.9 g, 59 mmol) indichloromethane (15 mL) was treated dropwise with DIPEA (12 mL, 66 mmol)followed by a solution of3-[4-(bromomethyl)-2-flurorphenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole(1.2 g, 3.7 mmol) in dichloromethane (5 mL). After 18 h, water wasintroduced (10 mL) and the reaction contents were extracted twice withdichloromethane and the combined organic layers were dried over sodiumsulfate and filtered. The resultant residue was purified by flashchromatography over silica gel (cyclohexane/EtOAc eluent gradient 1:0 to1:1) to afford1-[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-N-methoxy-methanamineas a colorless oil (410 mg, 38% yield). LC/MS (Method A) retentiontime=1.01 minutes, (M+H) not detected.

¹H NMR (400 MHz, CDCl₃) δppm: 8.05 (t, 1H), 7.45 (m, 2H), 5.85 (brs,1H), 4.12 (s, 2H), 3.50 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.21 (s), −107.33 (s).

Step 4: Preparation ofN-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-N,2-dimethoxy-propanamide

To a stirring solution of 2-methoxy propanoic acid (0.01 g, 0.08 mmol)and HATU (0.03 g, 0.08 mmol in DMF (0.35 mL) under an atmosphere ofnitrogen at room temperature was introducedN-ethyl-N-isopropyl-propan-2-amine (0.2 mL, 1.03 mmol). After 5 minutes,1-[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-N-methoxy-methanamine(0.02 g, 0.07 mmol) was added. After 2 hours, ethyl acetate and waterwere introduced and the layers were separated. The aqueous layer wasextracted with EtOAc and the combined organic phase was washed withbrine, dried over sodium sulfate, filtered and evaporated to dryness. Acrude white gum was purified by flash chromatography over silica gel(cycloheptane: EtOAc eluent gradient 99:1 to 1:1) to giveN-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-N,2-dimethoxy-propanamide(0.08 g, 35%) as a clear oil. LC/MS (Method A) retention time=1.02minutes, 378 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 8.06 (t, 1H), 7.25 (m, 2H), 4.96 (m, 1H),4.83 (m, 1H), 4.28 (q, 1H), 3.71 (s, 3H), 3.38 (s, 3H), 1.26 (d, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.21 (s), −106.58 (s).

Example 10

This example illustrates the preparation1-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1-methoxy-3-methyl-urea(Compound 3.45 of Table T1)

To a solution of1-[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-N-methoxy-methanamine(20 mg, 0.07 mmol) in DCM (0.23 mL, 0.07 mmol) was addedN-methylcarbamoyl chloride (0.012 g, 0.14 mmol) followed bytriethylamine (0.02 mL, 0.02 mmol). After 1 hour, the reaction mixturewas concentrated under reduced pressure and the residue was purified byflash chromatography over silica gel (cyclohexane: EtOAc eluent gradient99:1 to 1:1) to provide1-[[3-fluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-1-methoxy-3-methyl-urea(12 mg, 50% yield) as a gum. LC/MS (Method A) retention time=0.97minutes, 349 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 8.04 (t, 1H), 7.31 (m, 2H), 5.81 (m, 1H),4.71 (s, 2H), 3.60 (s, 3H), 2.87 (d, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.17 (s), −107.10 (s).

Example 11

This example illustrates the preparation2-chloro-N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-N-methoxy-benzamide(Compound 1.576 of Table T1)

Step 1: Preparation of 2,3-difluoro-N′-hydroxy-4-methyl-benzamidine

To a suspension of 2,3-difluoro-4-methylbenzonitrile (5.0 g, 32.6 mmol)in ethanol (111 mL) at 25° C. was added hydroxylamine hydrochloride (4.5g, 65.3 mmol). The reaction mixture was heated at 80° C. for 2 h. Aftercooling to room temperature the volatiles were removed under reducedpressure thus affording a white solid that was used in the next stepwithout purification.

¹H NMR (400 MHz, CDCl₃) δppm: 7.30 (m, 1H), 6.95 (m, 1H), 6.50 (brs,1H), 5.05 (brs, 2H), 2.30 (s, 3H).

Step 2: Preparation of3-(2,3-difluoro-4-methyl-phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole

To a solution of 2,3-difluoro-N′-hydroxy-4-methyl-benzamidine (2.6 mmol)in tetrahydrofuran (108 mL) cooled using an ice bath was added TFAA (6.9mL, 49 mmol). The reaction mixture was stirred at 25° C. overnight andthen diluted with water. The organic layer was separated, washedsuccessively with sodium bicarbonate solution, ammonium chloridesolution, and water then dried over sodium sulfate, filtered andevaporated to dryness. The crude title compound (6.6 g, 72% yield) wasisolated as a light brown solid that was used in the next transformationwithout further purification. LC/MS (Method A) retention time=1.16minutes, 265 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 7.76 (d, 1H), 7.12 (d, 1H), 2.41 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.41 (s), −133.3 (s), −140.1 (s).

Step 3: Preparation of3-[4-(bromomethyl)-2,3-difluoro-phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

A mixture of3-(2,3-difluoro-4-methyl-phenyl)-5-(trifluoromethyl)-1,2,4-oxadiazole(6.0 g, 22.6 mmol) and NBS (7.17 g, 10.0 mmol) in tetrachloromethane (79mL) under argon was heated to 70° C. AIBN (0.68 g, 3.95 mmol) was addedand the reaction mixture stirred at 65° C. for 36 h. The mixture wascooled to 25° C., diluted with dichloromethane and water, and the layerswere separated. The succinimide by-product was filtered off, and thesolvent was removed under vacuum, to afford a brown gum. This cruderesidue was subjected to flash chromatography over silica gel(cyclohexane/EtOAc eluent gradient 100:0 to 4:1) to afford the titlecompound as a white solid (4.8 g, 72% yield). LC/MS (Method A) retentiontime=1.16 minutes, 344 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 7.80 (m, 1H), 7.37 (m, 1H), 4.55 (s, 2H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.1 (s), −131.2 (s), −139.1 (s).

Step 4: Preparation of1-[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-N-methoxy-methanamine

A solution of O-methylhydroxylamine hydrochloride (3.5 g, 42 mmol) indichloromethane (8 mL) was treated dropwise with DIPEA (8.3 mL, 47 mmol)followed by a solution of3-[4-(bromomethyl)-2,3-difluoro-phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole(2 g, 5.2 mmol) in dichloromethane (5 mL). After 18 h, water wasintroduced (10 mL) and the reaction contents were extracted twice withdichloromethane and the combined organic layers were dried over sodiumsulfate and filtered. The resultant residue was purified by flashchromatography over silica gel (cyclohexane/EtOAc eluent gradient 1:0 to1:1) to afford1-[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-N-methoxy-methanamineas a pale yellow oil (1.1 g, 68% yield). LC/MS (Method A) retentiontime=1.03 minutes, 310 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 7.84 (t, 1H), 7.38 (t, 1H), 5.87 (brs,1H), 4.20 (s, 2H), 3.52 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.21 (s), −132.53 (s), −147.50 (s).

Step 5: Preparation2-chloro-N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-N-methoxy-benzamide

A clear solution of1-[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-N-methoxy-methanamine(0.150 g, 0.485 mmol) and DCM (3 mL) was treated with triethylamine(0.13 mL, 0.970 mmol) followed by 2-chlorobenzoyl chloride (80 mg, 0.51mmol). After 2 hr, isolute was added to the reaction mixture andvolatiles were removed under reduced pressure. The crude product wassubjected to flash chromatography over silica gel with cyclohexane/EtOAc99:1 to 1:1 to afford2-chloro-N-[[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]-N-methoxy-benzamide(212 mg, 98% yield) as a colourless oil. LC/MS (Method A) retentiontime=1.16 minutes, 448 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 7.88 (m, 1H), 7.54 (m, 1H), 7.40 (m, 4H),5.14 (brs, 2H), 3.52 (brs, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.21 (s), −131.98 (s), −141.10 (s).

Example 12

This example illustrates the preparationN-methoxy-N-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-pyridyl]methyl]cyclopropanecarboxamide(Compound 1.570 of Table T1)

Step 1: Preparation of N′-hydroxy-6-methyl-pyridine-3-carboxamidine

To a suspension of 5-cyano-2-picoline (3 g, 25.0 mmol) in ethanol (86mL) at 25° C. was added hydroxylamine hydrochloride (5.3 g, 76 mmol).The reaction mixture was heated at 80° C. for 2 h. After cooling to roomtemperature the volatiles were removed under reduced pressure thusaffording a white solid that was used in the next step without anypurification. LC/MS (Method A) retention time=0.17 minutes, 152 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 8.75 (s, 1H), 7.83 (d, 1H), 7.19 (d, 1H),4.86 (brs, 2H), 2.63 (s, 3H).

Step 2: Preparation of3-(6-methyl-3-pyridyl)-5-(trifluoromethyl)-1,2,4-oxadiazole

To a solution of N′-hydroxy-6-methyl-pyridine-3-carboxamidine (25 mmol)in tetrahydrofuran (84 mL) cooled via an ice bath was added TFAA (5.28mL, 38.0 mmol). The reaction mixture was stirred at 25° C. overnight andthen diluted with water. The organic layer was separated, washedsuccessively with sodium bicarbonate solution, ammonium chloridesolution, and water then dried over sodium sulfate, filtered andevaporated to dryness to afford3-(6-methyl-3-pyridyl)-5-(trifluoromethyl)-1,2,4-oxadiazole (5.8 g, 84%yield) as an amorphous white solid. LC/MS (Method A) retention time=1.14minutes, 247 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 9.23 (d, 1H), 8.27 (dd, 1H), 7.33 (d, 1H),2.63 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.3 (s).

Step 3: Preparation of3-[6-(bromomethyl)-3-pyridyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

A solution of3-(6-methyl-3-pyridyl)-5-(trifluoromethyl)-1,2,4-oxadiazole (4.4 g, 19mmol), AIBN (0.32 g, 1.9 mmol), and tetrachloromethane (38 mL) underargon was heated to 65° C. NBS (3.11 g, 17.1 mmol) was added portionwiseand the reaction mixture stirred at 65° C. for 5 h and then a secondequivalent of NBS (3.11 g, 17.1 mmol) and stirring continued overnight.The mixture was cooled to 25° C. then diluted with dichloromethane andwater after which the layers were separated. The succinimide by-productwas filtrated off, and the solvent was removed under reduced pressure toafford a brown gum. This crude residue was subjected to flashchromatography over silica gel (cyclohexane/EtOAc eluent gradient 100:0to 4:1) to afford3-[6-(bromomethyl)-3-pyridyl]-5-(trifluoromethyl)-1,2,4-oxadiazole as awhite solid (5.9 g, 37% yield. LC/MS (Method A) retention time=1.01minutes, 308 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 9.30 (d, 1H), 8.40 (dd, 1H), 7.63 (d, 1H),4.62 (s, 2H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.2 (s).

Step 4: Preparation ofN-methoxy-1-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-pyridyl]methanamine

A solution of O-methylhydroxylamine hydrochloride (4.4 g, 52 mmol) indichloromethane (26 mL) was treated dropwise with DIPEA (10.3 mL, 58mmol) followed by a solution of3346-(bromomethyl)-3-pyridyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (2 g,6.5 mmol) in dichloromethane (10 mL). After 18 h, additional equivalentsO-methylhydroxylamine hydrochloride (4.4 g, 52 mmol) and DIPEA (10.3 mL,58 mmol) were introduced and the reaction was heated at 40° C. for 48hr. of water was introduced (50 mL) and the reaction contents wereextracted twice with dichloromethane and the combined organic layerswere dried over sodium sulfate and filtered. The resultant residue waspurified by flash chromatography over silica gel (cyclohexane/EtOAceluent gradient 1:0 to 1:1) to afford1-[2,3-difluoro-4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]-N-methoxy-methanamineas a pale yellow solid (1.4 g, 79% yield). LC/MS (Method A) retentiontime=0.87 minutes, 275 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 9.31 (s, 1H), 8.37 (d, 1H), 7.52 (d, 1H),6.42 (brs, 1H), 4.24 (s, 2H), 3.56 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.25 (s).

Step 5: Preparation ofN-methoxy-N-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-pyridyl]methyl]cyclopropanecarboxamide

A clear solution ofN-methoxy-1-[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-pyridyl]methanamine(0.10 g, 0.36 mmol) and DCM (2 mL) cooled to 0° C. was treated withtriethylamine (0.10 mL, 0.73 mmol) followed by cyclopropanecarbonylchloride (38 mg, 0.36 mmol). After 2 hr, isolute was added to thereaction mixture and volatiles were removed under reduced pressure. Thecrude product was subjected to flash chromatography over silica gel(cyclohexane/EtOAc eluent gradient 99:1 to 1:1) to affordN-methoxy-N-[[5-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]-2-pyridyl]methyl]cyclopropanecarboxamide(212 mg, 98% yield) as a colourless oil. LC/MS (Method A) retentiontime=1.16 minutes, 448 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 7.88 (m, 1H), 7.54 (m, 1H), 7.40 (m, 4H),5.14 (brs, 2H), 3.52 (brs, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.21 (s), −131.98 (s), −141.10 (s).

Example 13

This example illustrates the preparation methylN-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]carbamate(Compound 2.3 of Table T2)

To a solution ofN-methoxy-1-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methanamine(0.10 g, 0.37 mmol) in DCM (1.2 mL) was added methyl chloroformate (0.06mL, 0.732 mmol) and triethylamine (0.10 mL, 0.73 mmol). The reactionmixture was stirred for 1 h 30 min at room temperature after which timethe solvent was removed under reduced pressure and the resultant cruderesidue was purified by combiflash chromatography over silica gel(cyclohexane/EtOAc eluent gradient 1:0 to 1:1) give methylN-methoxy-N-[[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]methyl]carbamate(0.105 g, 87% Yield) as a yellow oil. LC/MS (Method A) retentiontime=1.06 minutes, 332 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 8.04 (d, 2H), 7.42 (d, 2H), 4.64 (s, 2H),3.75 (s, 3H), 3.57 (s, 3H).

¹⁹F NMR (400 MHz, CDCl₃) δppm: −65.33 (s).

Example 14 Preparation ofN-Isopropyl-N-[2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]cyclopropanecarboxamide(Compound 1.810 of Table T1)

Step 1: Preparation of 4-(2-bromoethyl)-N′-hydroxy-benzamidine

To a stirring solution of 4-(2-bromoethyl)benzonitrile (5 g, 24 mmol) inethanol (80 mL) was added at room temperature triethylamine (15 mL, 110mmol) and hydroxylamine hydrochloride (3.3 g, 48 mmol). After 6 hoursthe solvent was evaporated under reduced pressure to afford the titlecompound as crude solid that was used without further purification.

Step 2: Preparation of3-[4-(2-bromoethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole

To a stirring suspension of crude4-(2-bromoethyl)-N′-hydroxy-benzamidine (24 mmol) in2-methyltetrahydrofuran (150 mL) was added TFAA (10 mL, 71 mmol) at 0°C. The reaction mixture was stirred at 25° C. for 15 hours and thendiluted with water (100 mL), followed by extraction with EtOAc. Theorganic layers were separated, washed successively with saturatedaqueous sodium bicarbonate solution and water, dried over sodiumsulfate, filtered and evaporated to dryness under reduced pressure. Thecrude residue was subject to flash chromatography oversilicagel(cyclohexane/EtOAc eluent gradient 95:5) to afford3-[4-(2-bromoethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (4.93 g,65% yield) as white solid m.p 39-40° C. LC/MS (Method A) retentiontime=1.19 minutes, mass not detected.

¹H NMR (400 MHz, CDCl₃) δppm: 8.07 (d, 2H), 7.37 (d, 2H), 3.61 (t, 2H),3.25 (t, 2H).

Step 3: Preparation ofN-[2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]propan-2-amine

To a stirring solution of3-[4-(2-bromoethyl)phenyl]-5-(trifluoromethyl)-1,2,4-oxadiazole (1.5 g,4.40 mmol) in dichloromethane (10 mL) was added dropwiseN-ethyl-N-isopropyl-propan-2-amine (0.76 mL, 4.40 mmol) at roomtemperature followed by the addition of isopropylamine (9.2 mL, 110mmol). The mixture was stirred at room temperature for 37 hours thenpoured into water and extracted three times with EtOAc. The combinedorganic layers were washed with brine, dried over sodium sulfate, andfiltered. The solvent was removed under reduced pressure and theresultant crude residue was purified by flash chromatography over silicagel (cyclohexane: EtOAc eluent gradient 98:2 to 95:5) to giveN-[2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]propan-2-amine(530 mg, 44% yield) as a clear oil. LC/MS (Method A) retention time=0.75minutes, minutes, 300.5 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 8.05 (d, 2H), 7.37 (d, 2H), 2.91 (m, 4H),2.85 (m, 1H), 1.06 (d, 6H).

Step 4: Preparation ofN-isopropyl-N-[2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]cyclopropanecarboxamide

To a stirring suspension ofN-[2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]propan-2-amine(0.075 g, 0.25 mmol) in dichloromethane (5 mL) under an atmosphere ofnitrogen was added triethylamine (0.04 mL, 0.30 mmol) at 0° C. followedby cyclopropanecarbonyl chloride (0.024 mL, 0.26 mmol). The reactionmixture was stirred at room temperature for 17 hours, poured into water,and extracted twice with EtOAc. The combined organic layers were washedwith brine, dried over sodium sulfate, and filtered. The solvent wasevaporated under reduced pressure and the resultant crude residue wassubjected to flash chromatography over silica gel (cyclohexane: EtOAceluent gradient 3:1 to 2:1) to affordN-isopropyl-N-[2-[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]phenyl]ethyl]cyclopropanecarboxamide(89 mg, 96% yield) as a white solid. LC/MS (Method A) retentiontime=1.17 minutes, minutes, 368.5 (M+H).

¹H NMR (400 MHz, CDCl₃) δppm: 8.06 (m, 2H), 7.38 (m, 2H), 4.79 (m,0.5H), 4.47 (m, 0.5H), 3.58 (m, 1H), 3.40 (m, 1H), 3.05 (m, 1H), 2.95(m, 1H), 1.76 (m, 1H), 1.29 (m, 3H), 1.13 (d, 3H), 1.04 (m, 1H), 0.83(m, 2H).

The following procedure was used in a combinatorial fashion usingappropriate building blocks (compounds (II) and (III)) to provide thecompounds of Formula (I) wherein R⁸ is —C(O)R⁹. The compounds preparedvia the following combinatorial protocol were analyzed using LC/MSMethod B.

By way of exemplification, acid derivatives of formula (III) (0.0375mmol in 375 μL DMA) were transferred to a 96 slot deep well plate(DWP96) containing the[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]aryl]methanamine derivativeof formula (II) (0.03 mmol) and DIPEA (0.09 mmol) in 250 μL DMA,followed by the addition of BOP-Cl (0.06 mmol) dissolved in DMA (250μL). The DWP was sealed and stirred at 50° C. for 18 hours. The solventwas removed under a stream of nitrogen. The resultant crude residueswere solubilized in a mixture of MeOH (250 μL) and DMA (500 μL) anddirectly submitted for preparative LC/MS purification which provided thecompounds of formula (I) in 10-85% yields.

Alternatively, the following procedures (protocol A and protocol B) wereused in a combinatorial fashion using appropriate building blocks(compounds (II) and (IV)) to provide the compounds of Formula (I)wherein R⁸ is —C(O)OR¹⁰ or —C(O)NR¹¹R¹². The compounds prepared via thefollowing combinatorial protocol were analyzed using LC/MS Method B.

Protocol A: Portions of triphosgene (6 mg) in DCE (0.3 mL) weretransferred at 0° C. to a 96 slot deep well plate (DWP96) containing thealcohol derivative [HOR¹⁰] or amine derivative [HN(R¹¹)R¹²] of formula(IV) (0.05 mmol) and triethylamine (0.12 mmol) in 200 μL DMA. Thereaction mixtures were stirred at room temperature for 30 minutes.[4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]aryl]methanaminederivatives of formula (II) (0.05 mmol) and triethylamine (0.12 mmol) in200 μL DMA were added. The DWP was sealed and stirred at roomtemperature for 18 hours. DCE was removed under the Barkey station. Thecrude residues were solubilized in a mixture of MeOH (200 μL) and DMA(600 μL) and directly submitted for preparative LC/MS purification whichprovided the compounds of formula (I) in 3-45% yields.

Protocol B: The alcohol derivative [HOR¹⁰] or amine derivative[HNR¹¹R¹²] of formula (IV) (0.05 mmol) and DIPEA (0.25 mmol) in 300 μLDMA were transferred at room temperature to a 96 slot deep well plate(DWP96). CDl (0.10 mmol) in DMA (300 μL) was added and stirred untilsolubilization.4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3-yl]aryl]methanamine derivativesof formula (II) (0.05 mmol) and triethylamine (0.12 mmol) in 200 μL DMAwere added. The DWP was sealed and stirred at room temperature for 18hours. The DCE was removed under the Barkey station. The crude residueswere solubilized in a mixture of MeOH (200 μL) and DMA (600 μL) anddirectly submitted for preparative LC/MS purification which provided thecompounds of formula (I) in 5-47% yields.

Where necessary, enantiomerically pure final compounds may be obtainedfrom racemic materials as appropriate via standard physical separationtechniques, such as reverse phase chiral chromatography, or throughstereoselective synthetic techniques, (eg, by using chiral startingmaterials).

TABLE T1 Melting point (mp) data and/or retention times (RT) forcompounds according to Formula (I): RT [M + Meth- MP Entry NameStructure (min) H] od (° C.) 1.1 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

0.99 316.3 A 1.2 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.07 342.3 A 35- 40 1.3 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.1 378.3 A 1.4 N-methoxy-2-phenyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.13 392.4 A 1.5 (E)-N-methoxy-3- phenyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- prop-2-enamide

1.17 404.4 A 94- 99 1.6 N-methoxy-1- (trifluoromethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-cyclopropane- carboxamide

1.89 410.2 B 1.7 N,2-dimethoxy- N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.79 408.2 B 1.8 2-cyclopentyl-N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

2.05 384.2 B 1.9 2,4-dichloro-N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

2.03 446.1 B 1.10 N-methoxy-2,2- dimethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pentanamide

2.16 386.3 B 1.11 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pent-4-ynamide

1.73 354.2 B 1.12 N-methoxy-2-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.82 344.2 B 1.13 N-methoxy-3- (trifluoromethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

2.01 446.2 B 1.14 N-methoxy-2,2,3,3- tetramethyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.18 398.3 B 1.15 2,2-difluoro-N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.79 378.2 B 1.16 N-methoxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclohexane- carboxamide

2.04 384.2 B 1.17 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pent-4-enamide

1.85 356.2 B 1.18 3-(4-chlorophenyl)-N- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

2.07 440.2 B 1.19 N-methoxy-1- (trifluoromethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane-carboxamide

2.01 424.2 B 1.20 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- hexanamide

2.03 372.2 B 1.21 1-(4-chlorophenyl)-N- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane-carboxamide

2.23 466.2 B 1.22 N-methoxy-2-methyl- 4-oxo-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pentanamide

1.70 386.2 B 1.23 N-methoxy-1-phenyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

2.00 418.2 B 1.24 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.82 344.2 B 1.25 N-methoxy-2-phenyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

2.02 418.2 B 1.26 2-cyclopropyl-N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.81 356.2 B 1.27 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentane- carboxamide

1.96 370.2 B 1.28 N-methoxy-2-(3- pyridyl)-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.25 393.2 B 1.29 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-3- carboxamide

1.62 372.2 B 1.30 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- thietane-3- carboxamide

1.80 374.2 B 1.31 N,3-dimethoxy-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.62 360.2 B 1.32 2,2-dichloro-N- methoxy-1-methyl-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.01 424.1 B 1.33 N-methoxy-1 -methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclohexane- carboxamide

2.21 398.3 B 1.34 N-methoxy-3-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.92 358.2 B 1.35 3-chloro-N-methoxy- 2,2-dimethyl-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.96 392.2 B 1.36 3,3,3-trifluoro-N- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.78 384.2 B 1.37 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyllmethyl]- naphthalene-1- carboxamide

1.96 428.2 B 1.38 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

1.86 356.2 B 1.39 N-methoxy-2-(4- phenylphenyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

2.13 468.3 B 1.40 N-methoxy-2-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.85 356.2 B 1.41 N-methoxy-3,3- dimethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.03 372.2 B 1.42 N-methoxy-2,2- dimethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.97 358.2 B 1.43 N-methoxy-1-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.81 356.2 B 1.44 2-chloro-N-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.88 412.1 B 1.45 N-methoxy-2-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- prop-2-enamide

1.74 342.2 B 1.46 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] tetrahydrothiopyran- 4-carboxamide

1.85 402.0 B 1.47 N-methoxy-2,2- dimethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.96 370.2 B 1.48 N-methoxy-2-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.92 358.2 B 1.49 2-(4-chlorophenyl)-N- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

2.00 426.2 B 1.50 N-methoxy-3-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3- carboxamide

1.61 372.2 B 1.51 3-fluoro-N-methoxy- 4-prop-2-ynoxy- N-[[4-[5-(trifluoromethy)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.88 450.2 B 1.52 2-(4-cyanophenyl)-N- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.80 417.2 B 1.53 6,6,6-trifluoro-N- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- hexanamide

1.96 426.2 B 1.54 N-[1-(methoxy-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] carbamoyl]-2-methyl- propyl]-cyclopropane- carboxamide

1.77 441.3 B 104.4- 109 1.55 6-bromo-N-methoxy- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,3-benzoxlioxole-5- carboxamide

1.88 500.1 B 1.56 3-(2,2-dibromovinyl)- N-methoxy-2,2-dimethyl-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- cyclopropane- carboxamide

2.24 552.1 B 1.57 N-methoxy-2- (methoxymethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.85 388.2 B 1.58 2-ethyl-N-methoxy-2- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.15 386.3 B 1.59 N,4-dimethoxy- N-[[4- (5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.69 374.2 B 1.60 2- (ethylsulfonylamino)- N-methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- pent-4-ynamide

1.82 461.2 B 1.61 2,2-dichloro-1-ethyl- N-methoxy-3- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.17 452.2 B 1.62 3-(2,2-dichlorovinyl)- N-methoxy-2,2-dimethyl-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- cyclopropane- carboxamide

2.22 464.2 B 1.63 3-(2,2-dichlorovinyl)- N-methoxy-2,2-dimethyl-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- cyclopropane- carboxamide

2.29 464.2 B 1.64 2-(2.2- difluorocyclopropyl)- N-methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.82 392.2 B 1.65 1-(3-chlorophenyl)-N- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.09 452.2 B 1.66 1-(2,4- difluorophenyl)-N- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.01 454.2 B 1.67 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,3- benzothiadiazole-7-carboxamide

1.93 436.2 B 1.68 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-2- [4-(trifluoromethyl)-phenyl]acetamide

2.03 460.2 B 1.69 2-(4-chlorophenyl)-N- methoxy-2-prop-2-ynoxy-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-acetamide

1.98 480.2 B 1.70 1-(4-ethoxyphenyl)- 2,2-difluoro-N- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2.4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.11 498.2 B 1.71 4-chloro-N-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.98 412.1 B 1.72 N-methoxy-1-(3- methoxyphenyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.97 448.2 B 1.156 N-isopropyl-2- methoxy-N-[2-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- acetamide

1.08 372 A 1.74 N-methoxy-1-(4- methoxyphenyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.96 448.2 B 1.75 1 -(4-chlorophenyl)- N-methoxy-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.10 452.2 B 1.76 N-methoxy-2,2- dimethyl-3-phenyl-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

2.18 434.3 B 1.77 prop-2-ynyl N-[1- [methoxy-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] carbamoyl]-2-methyl-propyl]carbamate

1.85 455.3 B 1.78 1 -(3-bromo-5-chloro- 2-pyridyl)-N- methoxy- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.13 531.1 B 1.79 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-2- (2,4,6- trimethylphenyl)-acetamide

2.16 434.3 B 1.80 N-methoxy-2-methyl- 3-phenyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

2.14 420.2 B 1.81 N,2-dimethoxy-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.62 360.2 B 62- 65 1.82 N-methoxy-3- (trifluoromethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- pentamide

2.05 426.2 B 1.83 N-cyclopropyl-1- (trifluoromethyl)- N-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-cyclopropane- carboxamide

1.93 419.1 B 1.84 2-cyclopentyl-N- cyclopropyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

2.13 394.3 B 1.85 N-cyclopropyl-2,2- dimethyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- pentanamide

2.18 396.3 B 1.86 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pent-4-ynamide

1.8 364.2 B 1.87 N-cyclopropyl-2- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.88 354.2 B 1.88 N-cyclopropyl-3- (trifluoromethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

2.06 456.2 B 1.89 N-cyclopropyl-2,2- difluoro-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.87 388.2 B 1.90 N-cyclopropyl-N- [[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclohexane- carboxamide

2.1 394.3 B 1.91 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pent-4-enamide

1.92 366.2 B 1.92 N-cyclopropyl-1- (trifluoromethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane-carboxamide

2.03 434.2 B 1.93 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- hexanamide

2.1 382.3 B 1.94 2-(2-chlorophenyl)-N- cyclopropyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

2.07 436.2 B 1.95 N-cyclopropyl-2- methyl-4-oxo-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- pentanamide

1.78 396.2 B 1.96 N-cyclopropyl-1- phenyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

2.09 428.2 B 1.97 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.89 354.2 B 1.98 N-cyclopropyl-2- phenyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

2.09 428.2 B 1.99 N,2-dicyclopropyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.88 366.2 B 1.100 N-cyclopropyl-N-[[4- [5-(trifIuoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentane- carboxamide

2.04 380.2 B 1.101 N-cyclopropyl-4,4,4- trifluoro-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.94 408.2 B 1.102 N-cyclopropyl-2-(3- pyridyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.3 403.2 B 1.103 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-3- carboxamide

1.68 382.2 B 1.104 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- thietane-3- carboxamide

1.85 384.2 B 1.105 N-cyclopropyl-2,6- dimethyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

2.07 416.2 B 1.106 N-cyclopropyl-3- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.71 370.2 B 1.107 2,2-dichloro-N- cyclopropyl-1-methyl- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.07 434.2 B 1.108 N-cyclopropyl-1- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclohexane- carboxamide

2.23 408.3 B 1.109 N-cyclopropyl-3- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2 368.2 B 1.110 3-chloro-N- cyclopropyl-2,2- dimethyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

2 402.2 B 1.111 N-cyclopropyl-3,3,3- trifluoro-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.84 394.2 B 1.112 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2.4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

1.94 366.2 B 1.113 N-cyclopropyl-2-(2- methoxyphenyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

2 432.2 B 1.114 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]pent- 3-enamide

1.92 366.2 B 1.115 N-cyclopropyl-2- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.93 366.2 B 1.116 N-cyclopropy 1-3,3- dimethyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.11 382.3 B 1.117 N-cyclopropyl-2,2- dimethyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.98 368.3 B 1.118 N-cyclopropyl-1- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.86 366.2 B 1.119 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.79 340.2 B 1.120 2-chloro-N- cyclopropyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.99 422.2 B 1.121 N-cyclopropyl-2- phenyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.97 402.2 B 1.122 N-cyclopropyl-2- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]prop- 2-enamide

1.82 352.2 B 1.123 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrothiopyran- 4-carboxamide

1.91 412.2 B 1.124 N-cyclopropyl-2,2- dimethyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.04 380.2 B 1.125 2,2-dichloro-N- cyclopropyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.02 420.1 B 1.126 N-cyclopropyl-2- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.98 368.2 B 1.127 2-(4-chlorophenyl)-N- cyclopropyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

2.07 436.2 B 1.128 N-cyclopropyl-3- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3- carboxamide

1.64 382.2 B 1.129 N-cyclopropyl-3- fluoro-4-prop-2- ynoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.92 460.2 B 1.130 2-(4-cyanophenyl)-N- cyclopropyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.87 427.2 B 1.131 N-cyclopropyl-6,6,6- trifluoro-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- hexanamide

2.02 436.2 B 1.132 N-[1-[cyclopropyl-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamoyl]-2- methyl-propyl]-cyclopropane- carboxamide

1.84 451.3 B 1.133 6-bromo-N- cyclopropyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-1,3- benzodioxole-5- carboxamide

1.98 510.1 B 1.134 N-cyclopropyl-2- (methoxymethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.95 398.3 B 1.135 N-cyclopropyl-2-ethyl- 2-methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.17 396.3 B 1.136 N-cyclopropyl-4- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.77 384.2 B 1.137 N-cyclopropyl-2- (ethylsulfonylamino)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]pent- 4-ynamide

1.72 471.2 B 1.138 N-cyclopropyl-2-(2,2- difluorocyclopropyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.88 402.2 B 1.139 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,2,3- benzothiadiazole-7-carboxamide

1.95 446.2 B 1.140 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-2- [4- (trifluoromethyl)-phenyl]acetamide

2.1 470.2 B 1.141 2-(4-chlorophenyl)-N- cyclopropyl-2-prop-2-ynoxy-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-acetamide

2.05 490.2 B 1.142 4-chloro-N- cyclopropyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

2.03 422.2 B 1.143 N-cyclopropyl-1-(4- methoxyphenyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.05 458.3 B 1.144 prop-2-ynyl N-[1- [cyclopropyl-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamoyl]-2-methyl- propyl]carbamate

1.91 465.3 B 1.145 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamide

1.71 382.2 B 1.146 2-cyano-N- cyclopropyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.62 351.2 B 1.147 N-cyclopropyl-2- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.68 370.2 B 1.148 N-cyclopropyl-3- (trifluoromethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- pentanamide

2.12 436.2 B 1.149 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.83 352.2 B 1.150 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.91 388.2 B 1.151 N-prop-2-ynyl-1- (trifluoromethyl)-N- [[4-[5-(trifIuoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-cyclopropane- carboxamide

1.9 418.2 B 1.152 2-cyclopentyl-N-prop- 2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

2.01 392.2 B 1.153 2,2-dimethyl-N-prop- 2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- pentanamide

2.11 394.3 B 1.154 N-prop-2-ynyl-N-[[4- [5-(trifluoromethyl)-1,2.4-oxadiazol-3- yl]phenyl]methyl]- pent-4-ynamide

1.72 362.2 B 1.155 2-methyl-N-prop-2- ynyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.79 352.2 B 1.156 N-isopropyl-2- methoxy-N-[2-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- acetamide

1.08 272 A 1.157 2,2-difluoro-N-prop-2- ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.77 386.2 B 1.158 N-prop-2-ynyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclohexane- carboxamide

1.99 392.2 B 1.159 N-prop-2-ynyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pent-4-enamide

1.83 364.2 B 1.160 3-(4-chlorophenyl)-N- prop-2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

2.04 448.2 B 1.161 N-prop-2-ynyl-1- (trifluoromethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane-carboxamide

2.01 432.2 B 1.162 N-prop-2-ynyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- hexanamide

2 380.2 B 1.163 2-(2-chlorophenyl)-N- prop-2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.96 434.2 B 1.164 2-methyl-4-oxo-N- prop-2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- pentanamide

1.7 394.2 B 1.165 N-prop-2-ynyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.8 352.2 B 1.166 2-phenyl-N-prop-2- ynyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.98 426.2 B 1.167 2-cyclopropyl-N-prop- 2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.79 364.2 B 1.168 N-prop-2-ynyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentane- carboxamide

1.93 378.2 B 1.169 4,4,4-trifluoro-N-prop- 2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.85 406.2 B 1.170 N-prop-2-ynyl-2-(3- pyridyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.26 401.2 B 1.171 N-prop-2-ynyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-3- carboxamide

1.61 380.2 B 1.172 N-prop-2-ynyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- thietane-3- carboxamide

1.78 382.2 B 1.173 3-methoxy-N-prop-2- ynyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.64 368.2 B 1.174 2,2-dichloro-1-methyl- N-prop-2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-cyclopropane- carboxamide

2.02 432.1 B 1.175 3-methyl-N-prop-2- ynyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.89 366.2 B 1.176 3-chloro-2,2-dimethyl- N-prop-2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.93 400.2 B 1.177 3,3,3-trifluoro-N-prop- 2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.76 392.2 B 1.178 N-prop-2-ynyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

1.85 364.2 B 1.179 2-(2-methoxyphenyl)- N-prop-2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.91 430.2 B 1.180 N-prop-2-ynyl-N-[[4- [5-(trifluoromethyl)-1,2.4-oxadiazol-3- yl]phenyl]methyl]- pent-3-enamide

1.83 364.2 B 1.181 2-methyl-N-prop-2- ynyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.82 364.2 B 1.182 2,2-dimethyl-N-prop- 2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.92 366.2 B 1.183 1-methyl-N-prop-2- ynyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.8 364.2 B 1.184 5-chloro-2-hydroxy-N- prop-2-ynyl-N-[[4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.8 436.2 B 1.185 N-prop-2-ynyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.7 338.2 B 1.186 2-phenyl-N-prop-2- ynyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.88 400.2 B 1.187 2-methyl-N-prop-2- ynyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- prop-2-enamide

1.76 350.2 B 1.188 N-prop-2-ynyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrothiopyran- 4-carboxamide

1.82 410.2 B 1.189 2,2-dimethyl-N-prop- 2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2.4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.93 378.2 B 1.190 2,2-dichloro-N-prop- 2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.92 418.1 B 1.191 2-methyl-N-prop-2- ynyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methy]- butanamide

1.88 366.3 B 1.192 3-methyl-N-prop-2- ynyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3- carboxamide

1.63 380.2 B 1.193 2-(4-cyanophenyl)-N- prop-2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.79 425.2 B 1.194 2-(methoxymethyl)-N- prop-2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.86 396.3 B 1.195 2-ethyl-2-methyl-N- prop-2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.1 394.3 B 1.196 4-methoxy-N-prop-2- ynyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.69 382.2 B 1.197 2-(2,2- difluorocyclopropyl)- N-prop-2-ynyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.79 400.2 B 1.198 prop-2-ynyl N-[2- methyl-1-[prop-2-ynyl- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-carbamoyl]propyl]- carbamate

1.84 463.3 B 1.199 2-cyano-N-prop-2- ynyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.55 349.2 B 1.200 2-methoxy-N-prop-2- ynyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.67 368.2 B 1.201 N-prop-2-ynyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.73 350.2 B 1.202 N-prop-2-ynyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.85 386.2 B 1.203 N- (cyclopropylmethyl)- 1-(trifluoromethyl)-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-cyclopropane- carboxamide

2.03 434.2 B 1.204 N- (cyclopropylmethyl)- 2,2-dimethyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- pentanamide

2.26 410.3 B 1.205 N- (cyclopropylmethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]pent- 4-ynamide

1.86 378.2 B 1.206 N- (cyclopropylmethyl)- 2-methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.94 368.3 B 1.207 N- (cyclopropylmethyl)- 2,2-difluoroN-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.91 402.2 B 1.208 N- (cyclopropylmethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pent-4-enamide

1.97 380.3 B 1.209 N- (cyclopropylmethyl)- 2-methyl-4-oxo-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl)methyl]- pentanamide

1.84 410.2 B 1.210 N- (cyclopropylmethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.94 368.2 B 1.211 2-cyclopropyl-N- (cyclopropylmethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.93 380.2 B 1.212 N- (cyclopropylmethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentane- carboxamide

2.08 394.3 B 1.213 N- (cyclopropylmethyl)- 4,4,4-trifluoro-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.99 422.2 B 1.214 N- (cyclopropylmethyl)- 2-(3-pyridyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.41 417.2 B 1.215 N- (cyclopropylmethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-3- carboxamide

1.75 396.2 B 1.216 N- (cyclopropylmethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- thietane-3- carboxamide

1.92 398.2 B 1.217 N- (cyclopropylmethyl)- 3-melhoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.78 384.2 B 1.218 N- (cyclopropylmethyl)- 3-methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.04 382.3 B 1.219 3-chloro-N- (cyclopropylmethyl)-2,2-dimethyl-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- propanamide

2.08 416.2 B 1.220 N- (cyclopropylmethyl)- 3,3,3-trifluoro-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.89 408.2 B 1.221 N- (cyclopropylmethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyctobutane- carboxamide

2 380.2 B 1.222 N- (cyclopropylmethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pent-3-enamide

2 380.2 B 1.223 N- (cyclopropylmethyl)- 2-methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2 380.2 B 1.224 N- (cyclopropylmethyl)- 3,3-dimethyl-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2 380.2 B 1.225 N- (cyclopropylmethyl)- 2,2-dimethyl-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

2 380.2 B 1.226 N- (cyclopropylmethyl)- 1-methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyctopropane-carboxamide

2 380.2 B 1.227 N- (cyclopropylmethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.84 354.2 B 1.228 N- (cyclopropylmethyl)- 2-phenyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

2.02 416.3 B 1.229 N- (cyclopropylmethyl)- 2-methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- prop-2-enamide

1.9 366.2 B 1.230 N- (cyclopropylmethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrothiopyran- 4-carboxamide

1.95 426.2 B 1.231 N- (cyclopropylmethyl)- 2,2-dimethyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.07 394.3 B 1.232 2.2-dichloro-N- (cyclopropylmethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.07 434.2 B 1.233 N- (cyclopropylmethyl)- 2-methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.03 382.3 B 1.234 2-(4-chlorophenyl)-N- (cyclopropylmethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

2.11 450.2 B 1.235 N- (cyclopropylmethyl)- 3-methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3-carboxamide

1.76 396.2 B 1.236 2-(4-cyanophenyl)-N- (cyclopropylmethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.91 441.2 B 1.237 N- (cyclopropylmethyl)- 2-(methoxymethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2 412.3 B 1.238 N- (cyclopropylmethyl)- 4-methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.83 398.2 B 1.239 N- (cyclopropylmethyl)- 2- (ethylsulfonylamino)-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-pent-4-ynamide

1.79 485.2 B 1.240 N- (cyclopropylmethyl)- 2-(2,2- difluorocyclopropyl)-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-acetamide

1.93 416.2 B 1.241 prop-2-ynyl N-[1- (cyclopropylmethyl- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-carbamoyl]-2-methyl- propyl]carbamate

1.97 479.3 B 1.242 N- (cyclopropylmethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamide

1.82 396.2 B 1.243 2-cyano-N- (cyclopropylmethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.69 365.2 B 1.244 1-cyano-N- (cyclopropylmethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.86 391.2 B 1.245 N- (cyclopropylmethyl)- 2-methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.79 384.2 B 1.246 N- (cyclopropylmethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.88 366.2 B 1.247 N- (cyclopropylmethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.98 402.2 B 1.248 N-methoxy-N-[1- [4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]but-2- ynamide

1.75 353.1 B 1.249 N-methoxy-N-[1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- tetrahydropyran-2- carboxamide

1.80 399.1 B 1.250 N-methoxy-N-[1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]but-2- enamide

1.83 355.1 B 1.251 2,2-difluoro-N- methoxy-N-[1-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]ethyl]- cyclopropane-carboxamide

1.86 391.1 B 1.252 4-chloro-3-fluoro-N- methoxy-N-[1-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]ethyl]but- 2-enamide

1.98 407.1 B 1.253 N,2-dimethoxy-N-(1- [4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- acetamide

1.63 359.1 B 1.254 N-methoxy-N-[1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- butanamide

1.90 357.1 B 1.255 N-methoxy-2-methyl- N-[1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]but-2- enamide

1.86 369.1 B 1.256 2-cyclopropyl-N- methoxy-N-[1-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]ethyl]- acetamide

1.89 369.1 B 1.257 N-methoxy-N-[1 (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]ethyl]- cyclopentane- carboxamide

2.05 383.1 B 1.258 N-methoxy-N-[1- [4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- cyclopentene-1- carboxamide

1.94 381.1 B 1.259 N-methoxy-N-[1- [4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- thietane-3- carboxamide

1.87 387.1 B 1.260 N,3-dimethoxy-N-[1- [4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- propanamide

1.71 373.1 B 1.261 N-methoxy-3-methyl- N-[1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- butanamide

2.00 371.1 B 1.262 N-methoxy-N-[1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]pheny1]ethyl]- cyclobutane- carboxamide

1.94 369.1 B 1.263 4,4,4-trifluoro-N- methoxy-N-[1-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]ethyl]but-2- enamide

1.97 409.1 B 1.264 2-ethoxy-N-methoxy- N-[1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- acetamide

1.73 373.3 B 1.265 N-methoxy-2-methyl- N-[1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- cyclopropane- carboxamide

1.91 369.1 B 1.266 N-methoxy-2-(2- methoxyethoxy)- N-[1-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]ethyl]- acetamide

1.64 403.1 B 1.267 N-methoxy-3,3- dimethyl-N-[1- [4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]ethyl]- butanamide

2.12 385.2 B 1.268 N-methoxy-1- methyl- N-[1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- cyclopropane- carboxamide

1.87 369.1 B 1.269 N-methoxy-N-[1- [4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]prop- 2-ynamide

2.31 339.1 B 1.270 [2-[methoxy-[1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- amino]- 2-oxo-ethyl] acetate

1.68 387.1 B 1.271 1-fluoro-N-methoxy- N-[1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- cyclopropane- carboxamide

1.87 373.1 B 1.272 N-methoxy-4-oxo-N- [1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]pent- 2-enamide

1.70 383.1 B 1.273 N-methoxy-N-[1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- tetrahydrofuran-2- carboxamide

1.73 385.1 B 1.274 1-cyano-N-methoxy- N-[1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- cyclopropane- carboxamide

1.76 380.1 B 1.275 2-fluoroN-methoxy- N-[1-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- cyclopropane- carboxamide

1.73 373.1 B 1.276 N-methoxy-N-[1- [4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]-1,3- dioxolane-2- carboxamide

1.65 387.1 B 1.277 3,3,3-trifluoro-N- methoxy-N-[1-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]ethyl]- propanamide

1.85 397.1 B 1.278 N-methoxy-N-[1- [4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]furan- 3-carboxamide

1.82 381.1 B 1.279 N-methoxy-N-[1- [4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- cyclopropane- carboxamide

1.82 355.1 B 1.280 N,4-dimethoxy-N-[1- [4-[5-(trifluoro- methyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- butanamide

1.77 387.1 B 1.281 N-methoxy-N-[1- [4-[5- (trifiuoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- pentanamide

2.01 371.1 B 1.282 N-propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]but- 2-ynamide

1.85 367.1 B 1.283 N-propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydropyran-2- carboxamide

1.91 413.2 B 1.284 2-methyl-N-propoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.99 371.1 B 1.285 N-propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]but- 2-enamide

1.92 369.1 B 1.286 2,2-difluoro-N- propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.94 405.1 B 1.287 2-methoxy-N- propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.73 373.1 B 1.288 N-propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.99 371.1 B 1.289 2-cyclopropyl-N- propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.98 383.1 B 1.290 N-propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentane- carboxamide

2.13 397.2 B 1.291 N-propoxy-N-[[4-[5- (trifiuoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentene-1- carboxamide

2.04 395.1 B 1.292 N-propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]pheny1]methyl]- thietane-3- carboxamide

1.96 401.1 B 1.293 3-methoxy-N- propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.81 387.1 B 1.294 3-methyl-N-propoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.08 385.2 B 1.295 N-propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

2.04 383.1 B 1.296 4,4,4-trifluoro-N- propoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]but- 2-enamide

2.06 423.1 B 1.297 2-ethoxy-N-propoxy- N-[[4-[5- (trifluoromethyl)-1,2.4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.83 387.1 B 1.298 2-(2-methoxyethoxy)- N-propoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.75 417.2 B 1.299 2-methyl-N-propoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

2.01 383.1 B 1.300 3,3-dimethyl-N- propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.19 399.2 B 1.301 N-propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- prop-2-enamide

1.85 355.1 B 1.302 1-methyl-N-propoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.98 383.1 B 1.303 N-propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.90 357.1 B 1.304 2-methyl-N-propoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- prop-2-enamide

1.91 369.1 B 1.305 N-propoxy-N-[[4-[5- (trifiuoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- prop-2-ynamide

1.79 353.1 B 1.306 [2-oxo-2-[propoxy- [[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]ethyl] acetate

1.77 401.1 B 1.307 1-fluoro-N-propoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.97 387.1 B 1.308 2-methyl-N-propoxy- N-[[4-[5- (trifiuoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.08 385.2 B 1.309 3-methyl-N-propoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3- carboxamide

1.79 399.1 B 1.310 4-oxo-N-propoxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pent-2-enamide

1.80 397.1 B 1.311 2-(methoxymethyl)- N- propoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.01 415.2 B 1.312 N-propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamide

1.81 399.1 B 1.313 1 -cyano-N-propoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.84 394.1 B 1.314 1-acetyl-N-propoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pyrrolidine-2- carboxamide

1.69 440.2 B 1.315 2-fluoro-N-propoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.83 387.1 B 1.316 2-methoxy-N- propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.80 387.1 B 1.317 N-propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,3-dioxolane-2- carboxamide

1.76 401.1 B 1.318 3,3,3-trifluoro-N- propoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.93 411.1 B 1.319 N-propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.92 369.1 B 1.320 N-propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.77 343.1 B 1.321 4-methoxy-N- propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.87 401.2 B 1.322 N-propoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pentanamide

2.09 385.2 B 1.323 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]but- 2-yaamide

1.65 368.3 B 1.324 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydropyran-2- carboxamide

1.73 413.2 B 1.325 N-(2-methoxyethyl)-2- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.73 372.3 B 1.326 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]but- 2-enamide

1.66 370.3 B 1.327 2,2-difluoro-N-(2- methoxyethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-cyclopropane- carboxamide

1.73 406.3 B 1.328 2-methoxy-N-(2- methoxyethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.51 374.3 B 1.329 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.74 372.3 B 1.330 N-(2-methoxyethyl)- 2- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- but-2-enamide

1.75 384.4 B 1.331 2-cyclopropyl-N-(2- methoxyethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.73 384.4 B 1.332 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentane- carboxamide

1.88 398.4 B 1.333 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentene-1- carboxamide

1.8 396.4 B 1.334 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenylmethyl]- thietane-3- carboxamide

1.73 402.3 B 1.335 3-methoxy-N-(2- methoxyethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.57 388.4 B 1.336 N-(2-methoxyethyl)-3- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.84 386.4 B 1.337 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

1.79 384.4 B 1.338 4,4,4-trifluoro-N-(2- methoxyethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]but- 2-enamide

1.83 424.3 B 1.339 2-ethoxy-N-(2- methoxyethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.61 388.4 B 1.340 2-(2-methoxyethoxy)- N-(2-methoxyethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.53 418.4 B 1.341 N-(2-methoxyethyl)-2- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.76 384.4 B 1.342 N-(2-methoxyethyl)- 3,3-dimethyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.95 400.4 B 1.343 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]prop- 2-enamide

1.59 356.3 B 1.344 N-(2-methoxyethyl)-1- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.73 384.3 B 1.345 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.62 358.3 B 1.346 N-(2-methoxyethyl)-2- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]prop- 2-enamide

1.69 370.3 B 1.347 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]prop- 2-ynamide

1.59 354.3 B 1.348 [2-[2-methoxyethyl- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]-2-oxo-ethyl] acetate

1.54 402.3 B 1.349 1-fluoro-N-(2- methoxyethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-cyctopropane- carboxamide

1.79 388.3 B 1.350 N-(2-methoxyethyl)-2- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.83 386.4 B 1.351 N-(2-methoxyethyl)-3- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-oxetane-3-carboxamide

1.56 400.4 B 1.352 N-(2-methoxyethyl)-4- oxo-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- pent-2-enamide

1.56 398.3 B 1.353 N-(2-methoxyethyl)- 2- (methoxymethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.81 416.4 B 1.354 1-formamido-N-(2- methoxyethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-cyclopropane- carboxamide

1.36 413.4 B 1.355 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamide

1.61 400.4 B 1.356 1-cyano-N-(2- methoxyethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-cyclopropane- carboxamide

1.68 395.3 B 1.357 1-acetyl-N-(2- methoxyethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-pyrrolidine-2- carboxamide

1.47 441.4 B 1.358 2-fluoro-N-(2- methoxyethyl)-N-[[4-[5-(trifIuoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-cyclopropane- carboxamide

1.61 388.3 B 1.359 2-methoxy-N-(2- methoxyethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.58 388.4 B 1.360 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,3-dioxolane-2- carboxamide

1.55 402.3 B 1.361 3,3,3-trifluoro-N-(2- methoxyethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.73 412.3 B 1.362 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- furan- 3-carboxamide

1.67 396.3 B 1.363 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.66 370.3 B 1.364 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.5 344.3 B 1.365 4-methoxy-N-(2- methoxyethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.62 402.4 B 1.366 N-(2-methoxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pentanamide

1.84 386.4 B 1.367 N-sec-butyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- but-2-ynamide

1.87 365.1 B 1.368 N-sec-butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydropyran-2- carboxamide

1.97 411.2 B 1.369 2-methyl-N-sec- butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.95 369.2 B 1.370 N-sec-butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl] but-2-enamide

1.88 367.2 B 1.371 2,2-difluoro-N-sec- butyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.92 403.1 B 1.372 2-methoxy-N-sec- bulyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.73 371.1 B 1.373 N-sec-butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.96 369.2 B 1.374 2-methyl-N-sec-butyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]but- 2-enamide

1.97 381.2 B 1.375 2-cyclopropyl-N-sec- butyl-N-[[4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.94 381.2 B 1.376 N-sec-butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentane- carboxamide

2.10 395.2 B 1.377 N-sec-butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentene-1- carboxamide

2.01 393.2 B 1.378 N-sec-butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- thietane-3- carboxamide

1.93 399.1 B 1.379 3-methoxy-N-sec- butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.80 385.2 B 1.380 3-methyl-N-sec-butyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.05 383.2 B 1.381 N-sec-butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

2.01 381.2 B 1.382 4,4,4-trifluoro-N-sec- butyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]but- 2-enamide

2.00 421.1 B 1.383 2-ethoxy-N-sec-butyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.83 385.2 B 1.384 2-(2-methoxyethoxy)- N-sec-butyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.74 415.2 B 1.385 2-methyl-N-sec-butyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.98 381.2 B 1.386 3,3-dimethyl-N-sec- butyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.16 397.2 B 1.387 N-sec-butyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- prop-2-enamide

1.81 353.1 B 1.388 1 -methyl-N-sec- butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.95 381.2 B 1.389 N-sec-butyl-N- [[4-[5- (trifiuoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.85 355.2 B 1.390 2-methyl-N-sec- butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- prop-2-enamide

1.90 367.2 B 1.391 N-sec-butyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- prop- 2-ynamide

1.81 351.1 B 1.392 [2-oxo-2-[sec-butyl- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]ethyl] acetate

1.74 399.1 B 1.393 1-fluoro-N-sec-butyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

2.00 385.1 B 1.394 2-methyl-N-sec-butyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.05 383.2 B 1.395 3-methyl-N-sec-butyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3- carboxamide

1.76 397.2 B 1.396 4-oxo-N-sec-butyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pent-2-enamide

1.76 395.1 B 1.397 2-(methoxymethyl)- N-sec-butyl-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.02 413.2 B 1.398 N-sec-butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamide

1.85 397.2 B 1.399 1-cyano-N-sec-butyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.86 392.1 B 1.400 1-acetyl-N-sec-butyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pyrrolidine-2- carboxamide

1.66 438.2 B 1.401 2-fluoro-N-sec-butyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.82 385.1 B 1.402 2-methoxy-N-sec- butyl-N-[[4-(5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.78 385.2 B 1.403 N-sec-butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,3-dioxolane-2- carboxamide

1.76 399.1 B 1.404 3,3,3-trifluoro-N-sec- butyl-N-[[4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenylmethyl]- propanamide

1.90 409.1 B 1.405 N-sec-butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- furan- 3-carboxamide

1.87 393.1 B 1.406 N-sec-butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.90 367.2 B 1.407 N-sec-butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.73 341.1 B 1.408 4-methoxy-N-sec- butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.85 399.2 B 1.409 N-sec-butyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pentanamide

2.05 383.2 B 1.410 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- 2-ynamide

1.73 394.3 B 1.411 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-tetrahydropyran-2- carboxamide

1.8 440.4 B 1.412 2-methyl-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.8 398.4 B 1.413 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]but- 2-enamide

1.74 396.4 B 1.414 2,2-difluoro-N- (tetrahydrofuran-2-ylmethyl)-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- cyclopropane- carboxamide

1.79 432.4 B 1.415 2-methoxy-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.59 400.3 B 1.416 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.81 398.4 B 1.417 2-methyl-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]but- 2-enamide

1.83 410.4 B 1.418 2-cyclopropyl-N- (tetrahydrofuran-2-ylmethyl)-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- acetamide

1.8 410.4 B 1.419 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentane-carboxamide

1.95 424.4 B 1.420 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentene-1-carboxamide

1.87 422.4 B 1.421 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- thietane-3-carboxamide

1.8 428.4 B 1.422 3-methoxy-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.65 414.4 B 1.423 3-methyl-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.91 412.4 B 1.424 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane-carboxamide

1.86 410.4 B 1.425 4,4,4-trifluoro-N- (tetrahydrofuran-2-ylmethyl)-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- but-2-enamide

1.9 450.4 B 1.426 2-ethoxy-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.69 414.4 B 1.427 2-(2-methoxyethoxy)- N-(tetrahydrofuran-2-ylmethyl)-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- acetamide

1.61 444.4 B 1.428 2-methyl-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.84 410.4 B 1.429 3,3-dimethyl-N- (tetrahydrofuran-2-ylmethyl)-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- butanamide

2.02 426.4 B 1.430 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- prop-2-enamide

1.67 382.3 B 1.431 1-methyl-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.81 410.4 B 1.432 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.71 384.3 B 1.433 2-methyl-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- prop-2-enamide

1.77 396.4 B 1.434 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl] prop-2-ynamide

1.67 380.3 B 1.435 [2-oxo-2- [tetrahydrofuran-2- ylmethyl-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]ethyl]acetate

1.62 428.4 B 1.436 1-fluoro-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.88 414.4 B 1.437 2-methyl-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.9 412.4 B 1.438 3-methyl-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl)methyl]- oxetane-3-carboxamide

1.64 426.4 B 1.439 4-oxo-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- pent-2-enamide

1.64 424.4 B 1.440 2-(methoxymethyl)-N- (tetrahydrofuran-2-ylmethyl)-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- butanamide

1.87 442.4 B 1.441 1-formamido-N- (tetrahydrofuran-2-ylmethyl)-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- cyclopropane- carboxamide

1.45 439.4 B 1.442 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-tetrahydrofuran-2- carboxamide

1.68 426.4 B 1.443 1-cyano-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.76 421.4 B 1.444 1-acetyl-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- pyrrolidine-2-carboxamide

1.54 467.4 B 1.445 2-fluoro-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.69 414.4 B 1.446 2-methoxy-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.65 414.4 B 1.447 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-1,3-dioxolane-2- carboxamide

1.63 428.4 B 1.448 3,3,3-trifluoro-N- (tetrahydrofuran-2-ylmethyl)-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- propanamide

1.8 438.4 B 1.449 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-furan-3-carboxamide

1.75 422.3 B 1.450 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.75 396.4 B 1.451 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetate

1.58 370.3 B 1.452 4-methoxy-N- (tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.7 428.4 B 1.453 N-(tetrahydrofuran-2- ylmethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- pentanamide

1.92 412.4 B 1.454 N-methoxy-2- (trifluoromethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.15 446.3 1.455 N-(2-furylmethyl)-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentane- carboxamide

2.01 420.3 B 1.456 N-(2-furylmethyl)-3- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.73 410.3 B 1.457 N-(2-furylmethyl)-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.78 380.3 B 1.458 N-(2-furylmethyl)-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

1.93 406.3 B 1.459 N-(2-furylmethyl)-2- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.67 396.3 B 1.460 N-(2-furylmethyl)-2- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.9 406.3 B 1.461 2-acetamido-N-(2- furylmethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.5 423.3 B 1.462 2-chloro-N-(2- furylmethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.77 400.2 B 1.463 N-(2-furylmethyl)-2- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.87 394.3 B 1.464 2,2-difluoro-N-(2- furylmethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.85 428.3 B 1.465 N-(2-furylmethyl)-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.88 394.3 B 1.466 N-(2-furylmethyl)-2- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyllmethyl]- butanamide

1.96 408.3 B 1.467 N-(2-furylmethyl)-4- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.77 424.3 B 1.468 N-(2-furylmethyl)-3- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3-carboxamide

1.7 422.3 B 1.469 N-(2-furylmethyl)-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamide

1.77 422.3 B 1.470 2-cyano-N-(2- furylmethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.64 391.4 B 1.471 2-fluoro-N-(2- furylmethyl)-N-[[4-(5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.75 410.3 B 1.472 N-(2-furylmethyl)-2- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.74 410.3 B 1.473 N-(2-furylmethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,3-dioxolane-2- carboxamide

1.7 424.3 B 1.474 N-(2-furylmethyl)-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.82 392.3 B 1.475 N-allyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentane- carboxamide

1.99 380.3 B 1.476 N-allyl-3-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.68 370.3 B 1.477 N-allyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.74 340.3 B 1.478 N-allyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

1.9 366.3 B 1.479 N-allyl-2-methoxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.61 356.3 B 1.480 N-allyl-2-methyl-N- [[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.88 366.3 B 1.481 2-acetamido-N-allyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.43 383.3 B 1.482 N-allyl-2-chloro-N- [[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.73 360.2 B 1.483 N-allyl-2-methyl-N- [[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.84 354.3 B 1.484 N-allyl-2,2-difluoro- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.82 388.3 B 1.485 N-allyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.85 354.3 B 1.486 N-allyl-2-methyl-N- [[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.94 368.3 B 1.487 N-allyl-4-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.73 384.3 B 1.488 N-allyl-3-methyl-N- [[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3- carboxamide

1.65 382.3 B 1.489 N-allyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamide

1.72 382.3 B 1.490 N-allyl-2-cyano-N- [[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.58 351.3 B 1.491 N-allyl-2-fluoro-N- [[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.71 370.3 B 1.492 N-allyl-2-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.69 370.3 B 1.493 N-allyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,3-dioxolane-2- carboxamide

1.65 384.3 B 1.494 N-allyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.78 352.3 B 1.495 N-ethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentane- carboxamide

1.93 368.3 B 1.496 N-ethyl-3-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.61 358.3 B 1.497 N-ethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.67 328.3 B 1.498 N-ethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobulane- carboxamide

1.84 354.3 B 1.499 N-ethyl-2-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.54 344.3 B 1.500 N-ethyl-2-methyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.82 354.3 B 1.501 2-acetamido-N-ethyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.37 371.3 B 1.502 2-chloro-N-ethyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.66 348.2 B 1.503 N-ethyl-2-methyl-N- [4-[5- (trifluoromethyl)-1,2.4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.78 342.3 B 1.504 N-ethyl-2,2-difluoro- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.76 376.3 B 1.505 N-ethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.78 342.3 B 1.506 N-ethyl-2-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.88 356.3 B 1.507 N-ethyl-4-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.67 372.3 B 1.508 N-ethyl-3-methyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3- carboxamide

1.58 370.3 B 1.509 N-ethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamide

1.64 370.3 B 1.510 2-cyano-N-ethyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.51 339.3 B 1.511 N-ethyl-2-fluoro-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.64 358.3 B 1.512 N-ethyl-2-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.61 358.3 B 1.513 N-ethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,3-dioxolane-2- carboxamide

1.58 372.3 B 1.514 N-ethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.72 340.3 B 1.515 N-methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopentane- carboxamide

1.83 354.3 B 1.516 3-methoxy-N-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.50 344.3 B 1.517 N-methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.56 314.3 B 1.518 N-methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

1.74 340.3 B 1.519 2-methoxy-N-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.43 330.3 B 1.520 N,2-dimethyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.72 340.3 B 1.521 2-acetamido-N- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.27 357.3 B 1.522 2-chloro-N-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.56 334.2 B 1.523 2,2-difluoro-N-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.66 362.2 B 1.524 N-methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.68 328.3 B 1.525 N.2-dimethyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.78 342.3 B 1.526 4-methoxy-N-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.56 358.3 B 1.527 N,3-dimethyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3- carboxamide

1.48 356.3 B 1.528 N-methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamide

1.53 356.3 B 1.529 2-fluoro-N-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.54 344.3 B 1.530 2-methoxy-N-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.51 344.3 B 1.531 N-methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- 1,3-dioxolane-2- carboxamide

1.47 358.3 B 1.532 N-methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.61 326.3 B 1.533 N-(3,3- dichloroallyloxy)-3- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.92 454.3 B 1.534 N-(3,3- dichloroallyloxy)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

2 424.2 B 1.535 N-(3,3- dichloroallyloxy)-2- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.85 440.2 B 1.536 N-(3,3- dichloroallyloxy)-2- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.1 450.3 B 1.537 2-acetamido-N-(3,3- dichloroallyloxy)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.65 467.2 B 1.538 2-chloro-N-(3,3- dichloroallyloxy)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.96 444.2 B 1.539 N-(3,3- dichloroallyloxy)-2- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

2.08 438.2 B 1.540 N-(3,3- dichloroallyloxy)- 2,2- difluoro-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.02 472.2 B 1.541 N-(3,3- dichloroallyloxy)- N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.08 438.2 B 1.542 N-(3,3- dichloroallyloxy)-2- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.16 452.2 B 1.543 N-(3,3- dichloroallyloxy)-4- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.97 468.3 B 1.544 N-(3,3- dichloroallyloxy)-3- methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3-carboxamide

1.9 466.2 B 1.545 N-(3,3- dichloroallyloxy)-2- fluoro-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.93 454.2 B 1.546 N-(3,3- dichloroallyloxy)-2- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.91 454.2 B 1.547 N-(3,3- dichloroallyloxy)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyllmethyl]-1,3-dioxolane-2- carboxamide

1.88 468.2 B 1.548 N-(3,3- dichloroallyloxy)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.02 436.2 B 1.549 N-[(4- chlorophenyl)- methoxy]- 3-methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.98 470.3 B 1.550 N-[(4- chlorophenyl)- methoxy]- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

2.05 440.3 B 1.551 N-[(4- chlorophenyl)- methoxy]- 2-methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.91 456.3 B 1.552 2-ace tamido-N-[(4- chlorophenyl)- methoxy]-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-acetamide

1.73 483.3 B 1.553 2-chloro-N-[(4- chlorophenyl)- methoxy]- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

2.01 460.2 B 1.554 N-[(4- chlorophenyl)- methoxy]- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.13 454.3 B 1.555 N-[(4- chlorophenyl)- methoxy]- 4-methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.02 484.3 B 1.556 N-[(4- chlorophenyl)- methoxy]- 3-methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3-carboxamide

1.96 482.3 B 1.557 N-[(4- chlorophenyl)- methoxy]- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-tetrahydrofuran-2- carboxamide

1.99 482.3 B 1.558 N-[(4- chlorophenyl)- methoxy]- 2-fluoro-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.99 470.3 B 1.559 N-[(4- chlorophenyl)- methoxy]- 2-methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl)methyl]- propanamide

1.97 470.3 B 1.560 N-[(4- chlorophenyl)- methoxy]- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-1,3-dioxolane-2- carboxamide

1.94 484.3 B 1.561 N-[(4- chlorophenyl)- methoxy]- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

2.05 452.3 B 1.562 N-ethoxy-N-[[4-[5- (trifiuoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.76 344.15 B 1.563 N-[[2-fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-N- methoxy- tetrahydrofuran-2-carboxamide

1.06 390 A 1.564 N-ethoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.79 356.15 B 1.565 2-chloro-N-[[2- fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- N-methoxy- benzamide

1.17 430 A 1.566 N-[[2-fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- N-methoxy- cyclopropane-carboxamide

1.11 360 A 1.567 N-ethoxy-2- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.60 360.14 B 1.568 N-[[2-fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- N-methoxy- propanamide

1.1 348 A 1.569 N-methoxy-N-[[5- [5- (trifiuoromethyl)-1,2,4-oxadiazol-3- yl]-2- pyridyl]methyl]- tetrahydrofuran-2-carboxamide

0.94 373 A 1.570 N-methoxy-N-[[5- [5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]-2- pyridyl]methyl]- cyclopropane- carboxamide

0.99 343 A 1.571 N-methoxy-N-[[5- [5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]-2- pyridyl]methyl]- propanamide

0.97 331 A 1.572 2-chloro-N-methoxy- N-[[5-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]-2- pyridyl]methyl]- benzamide

80- 89 1.573 N-propyl-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- propanamide

1.77 342.19 B 1.574 N-propyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.82 354.18 B 1.575 2-methoxy-N-propyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.63 358.18 B 1.576 2-chloro-N-[[2,3- difluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-N- methoxy-benzamide

1.16 448 A 1.577 N-[[2,3-difluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-N- methoxy- tetrahydrofuran-2-carboxamide

1.08 408 A 1.578 N-[[3-fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-N- methoxy- tetrahydrofuran-2-carboxamide

1.04 391 A 1.579 N-[[3-fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-N- methoxy- cyclopropane-carboxamide

1.06 360 A 1.580 N-[[3-fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-N- methoxy- propanamide

1.05 348 A 1.581 2-chloro-N-[[3-fluoro- 4-[5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-N- methoxy-benzamide

89- 95 1.582 N-(2,2,2- trifluoroethyl)-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.78 382.15 B 1.583 2-methoxy-N-(2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

92.6- 94.3 1.584 N-[[2,3-difluoro- 4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- N-methoxy- cyclopropane-carboxamide

1.11 378 A 1.585 N-[[2,3-difluoro- 4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl)phenyl]methyl)- N-methoxy- propanamide

1.09 366 A 1.586 N-(2,2,2- trifluoroethyl)-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.81 394.14 B 1.587 N-(2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-tetrahydrofuran-2- carboxamide

1.80 424.17 B 1.588 N-butoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

2.00 372.20 B 1.589 N-isopropyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.74 342.19 B 1.590 2-[propanoyl-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]ethyl propanoate

1.08 400 A 1.591 N-(2-hydroxyethyl)- N-[[4-[5- (trifiuoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.34 344.15 B 1.592 N-allyl-N-[cyano- [4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.11 365.3 A 1.593 2-hydroxy-N- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

54- 60 1.594 N-[[2,6-difluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- N-methoxy- propanamide

1.12 366 A 1.595 2-(difluoromethoxy)- N-methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.02 366 A 1.596 N-[[2,6-difluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-N- methoxy- cyclopropane-carboxamide

1.13 378 A 1.597 N-[[2,6-difluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl)-N- methoxy- tetrahydrofuran-2-carboxamide

1.08 408 A 1.598 2-chloro-N-[[2,6- difluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-N- methoxy-benzamide

1.19 448 A 1.599 N-isopropyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.79 354.18 B 1.600 N-isopropyl-2- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.60 358.18 B 1.601 N-butoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

2.02 384.20 B 1.602 N-butoxy-2-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.83 388.18 B 1.603 N-hydroxy-N-[[4-[5- (trifiuoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.39 316.12 B 141.2- 143.5 1.604 N-(oxetan-3-yl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

88.8- 93.5 1.605 N-(oxetan-3-yl)-N- [[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

89.5- 94 1.606 N-hydroxy-2- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

144.4- 147.8 1.607 N-hydroxy-N-[[4-[5- (trifiuoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

141.2- 143.5 1.608 [cyclopropanecarbonyl- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]- cyclopropane- carboxylate

1.79 396.16 B 1.609 N-(2-hydroxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.38 356.16 B 1.610 N-(2-hydroxyethyl)- 2-methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.24 360.16 B 1.611 N-[cyano-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-N- methyl-propanamide

75- 76 1.612 N-[cyano-[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl)-N- methyl- cyclopropane- carboxamide

1.08 351 A 1.613 2-methoxy-N- (oxetan- 3-yl)-N-[[4-[5-(trifluoromelhyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.28 372.15 B 1.614 N-ethoxy-2-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.87 358.17 B 1.615 N-ethoxy-2,2-difluoro- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.83 392.14 B 1.616 2-chloro-N-ethoxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.92 426.13 B 1.617 N-ethoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-3- carboxamide

1.66 386.17 B 1.618 N-ethoxy-3-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.67 374.17 B 1.619 N-ethoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

1.91 370.17 B 1.620 N-ethoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyctobutane- carboxamide

1.90 370.17 B 1.621 N-ethoxy-1-methyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.86 370.17 B 1.622 N-ethoxy-2-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.97 372.19 B 1.623 N-ethoxy-3-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3- carboxamide

1.66 386.16 B 1.624 N-ethoxy-2- (methoxymethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.89 402.21 B 1.625 N-ethoxy-4-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.74 388.19 B 1.626 N-ethoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamide

1.68 386.17 B 1.627 2-cyano-N-ethoxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl)phenyl]methyl]- acetamide

1.59 355.14 B 1.628 1-cyano-N-ethoxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.73 381.15 B 1.629 N-ethoxy-2-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.67 374.17 B 1.630 N-ethoxy-3,3,3- trifluoro-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.82 398.16 B 1.631 N-ethoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.62 330.13 B 1.632 2-cyclopropyl-N- ethoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.86 370.18 B 1.633 N-butoxy-2-methyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

2.09 386.22 B 1.634 N-butoxy-2,2-difluoro- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

2.03 420.19 B 1.635 N-butoxy-2-chloro-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

2.11 454.18 B 1.636 N-butoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-3- carboxamide

1.89 414.22 B 1.637 N-butoxy-3-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.91 402.21 B 1.638 N-butoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl] phenyl]methyl]- cyclobutane- carboxamide

2.13 398.22 B 1.639 N-butoxy-1-methyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

2.08 398.23 B 1.640 N-butoxy-2-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.18 400.24 B 1.641 N-butoxy-3-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3- carboxamide

1.88 414.22 B 1.642 N-butoxy-2- (methoxymethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

2.10 430.26 B 1.643 N-butoxy-4-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.96 416.24 B 1.644 N-butoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamide

1.91 414.22 B 1.645 N-butoxy-2-cyano-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.81 383.18 B 1.646 N-butoxy-1-cyano-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.93 409.20 B 1.647 N-butoxy-2-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.90 402.23 B 1.648 N-butoxy-3,3,3- trifluoro-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

2.02 426.19 B 1.649 N-butoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.87 358.18 B 1.650 N-butoxy-2- cydopropyl-N-[[4- [5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

2.07 398.22 B 1.651 2-methyl-N-propyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.88 356.23 B 1.652 2,2-difluoro-N- propyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.85 390.18 B 1.653 2-chloro-N-propyl- N-[[4-[5- (trifiuoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.99 424.17 B 1.654 N-propyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-3- carboxamide

1.68 384.20 B 1.655 3-methoxy-N-propyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.71 372.20 B 1.656 N-propyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

1.94 368.20 B 1.657 2-methyl-N-propyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.91 368.21 B 1.658 1-methyl-N-propyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.87 368.20 B 1.659 2-methyl-N-propyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.97 370.23 B 1.660 3-methyl-N-propyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3- carboxamide

1.67 384.20 B 1.661 2-(methoxymethyl)- N-propyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.94 400.24 B 1.662 4-methoxy-N-propyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.76 386.22 B 1.663 N-propyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]pheny1]methyl]- tetrahydrofuran-2- carboxamide

1.74 384.20 B 1.664 2-cyano-N-propyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.61 353.16 B 1.665 1 -cyano-N-propyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.79 379.18 B 1.666 2-methoxy-N-propyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.71 372.19 B 1.667 3,3,3-trifluoroN- propyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.82 396.18 B 1.668 N-propyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.63 328.17 B 1.669 2-cyclopropyl-N- propyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.87 368.21 B 1.670 N-isopropyl-2-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.84 356.21 B 1.671 2,2-difluoro-N- isopropyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.82 390.18 B 1.672 2-chloro-N-isopropyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.97 424.17 B 1.673 N-isopropyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-3- carboxamide

1.65 384.21 B 1.674 N-isopropyl-3- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.68 372.20 B 1.675 N-isopropyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

1.91 368.21 B 1.676 N-isopropyl-2- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.88 368.21 B 1.677 N-isopropyl-1- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.84 368.21 B 1.678 N-isopropyl-2- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.94 370.22 B 1.679 N-isopropyl-3- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3- carboxamide

1.63 384.21 B 1.680 N-isopropyl-2- (methoxymethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.92 400.24 B 1.681 N-isopropyl-4- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.73 386.22 B 1.682 N-isopropyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamide

1.71 384.20 B 1.683 2-cyano-N-isopropyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.58 353.17 B 1.684 1 cyano-N-isopropyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.75 379.18 B 1.685 N-isopropyl-2- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.68 372.20 B 1.686 3,3,3-trifluoro-N- isopropyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.80 396.18 B 1.687 N-isopropyl-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.60 328.16 B 1.688 2-cycloopropyl-N- isopropyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.84 368.20 B 1.689 2-methyl-N-(2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.87 396.18 B 1.690 2,2-difluoro-N-(2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.83 430.20 B 1.691 2-chloro-N-(2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.98 464.13 B 1.692 N-(2.2.2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-tetrahydrofuran-3- carboxamide

1.69 424.17 B 1.693 3-methoxy-N-(2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.73 412.16 B 1.694 N-(2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane-carboxamide

1.93 408.17 B 1.695 2-methyl-N-(2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.90 408.18 B 1.696 1-methyl-N-(2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.90 408.12 B 1.697 2-methyl-N-(2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.96 410.19 B 1.698 3-methyl-N-(2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3-carboxamide

1.71 424.33 B 1.699 2-(methoxymethyl)- N-(2,2,2- trifluoroethyl)-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-butanamide

1.96 440.20 B 1.700 4-methoxy-N-(2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.78 426.20 B 1.701 2-cyano-N-(2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.62 393.46 B 1.702 1-cyano-N-(2,2,2- trrfluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.79 419.26 B 1.703 2-methoxy-N- (2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.75 412.16 B 1.704 3,3,3-trifluoro-N- (2,2,2- trifluoroethyl)-N-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-propanamide

1.82 436.13 B 1.705 N-(2,2,2- trifluoroethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.65 368.12 B 1.706 2-cyclopropyl-N- (2,2,2- trifluoroethyl)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.87 408.16 B 1.707 N-(2-hydroxyethyl)- 2-methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.44 358.17 B 1.708 2,2-difluoro-N-(2- hydroxyethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-cyclopropane- carboxamide

1.46 392.14 B 1.709 2-chloro-N-(2- hydroxyethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.59 426.14 B 1.710 2-[(2-chlorobenzoyl)- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]ethyl 2- chlorobonzoato

2.07 564.15 B 1.711 N-(2-hydroxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-3- carboxamide

1.28 386.17 B 1.712 2-(tetrahydrofuran-3- carbonyl-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]ethyltetrahydrofuran-3- carboxylate

1.50 484.24 B 1.713 N-(2-hydroxyethyl)- 3- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.30 374.17 B 1.714 N-(2-hydroxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

1.50 370.17 B 1.715 2- [cyclobulanecarbonyl- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]ethyl cyclobutane-carboxylate

1.97 452.23 B 1.716 2-[(2-methoxy- acetyl)- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]ethyl 2- methoxyacetate

1.42 432.20 B 1.717 N-(2-hydroxyethyl)- 2-methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.49 370.18 B 1.718 N-(2-hydroxyethyl)- 1-methyl-N-[[4-[5-(trifiuoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyctopropane-carboxamide

1.45 370.17 B 1.719 N.2-dimethoxy-N- [[6-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]-3- pyridyl]methyl]- propanamide

0.88 361.5 A 1.720 N-(2-hydroxyethyl)- 2-methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.54 372.20 B 1.721 N-(2-hydroxyethyl)- 3-methyl-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3-carboxamide

1.28 386.17 B 1.722 2-[(3-methyloxetane- 3-carbonyl)-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]ethyl 3-methyloxetane-3- carboxylate

1.51 484.23 B 1.723 N-(2-hydroxyethyl)- 2-(methoxymethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.51 402.21 B 1.724 N-(2-hydroxyethyl)- 4-methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.35 388.19 B 1.725 2-[4- methoxybutanoyl-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]ethyl 4- methoxybutanoate

1.66 488.28 B 1.726 N-(2-hydroxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamido

1.34 386.18 B 1.727 2-[tetrahydrofuran-2- carbonyl-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]ethyltetrahydrofuran-2- carboxylate

1.60 484.23 B 1.728 2-cyano-N-(2- hydroxyethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.25 355.14 B 1.729 1-cyano-N-(2- hydroxyethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-cyclopropane- carboxamide

1.40 381.16 B 1.730 2-[(1- cyanocyclopropane- carbonyl)- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]ethyl 1-cyanocyclopropane- carboxylate

1.66 474.21 B 1.731 N-(2-hydroxyethyl)- 2-methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.30 374.18 B 1.732 2-[2- methoxypropanoyl- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]ethyl 2- methoxypropanoate

1.59 460.24 B 1.733 3,3,3-trifluoro-N-(2- hydroxyethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.47 398.15 B 1.734 2-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl- (3,3,3- trifluoropropanoyl)- amino]ethyl 3,3,3-trifluoropropanoate

1.47 508.16 B 1.735 N-(2-hydroxyethyl)- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.23 330.14 B 1.736 2-cyclopropyl-N-(2- hydroxyethyl)-N-[[4-[5-(trifIuoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.46 370.17 B 1.737 2-[(2- cyclopropylacetyl)- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]ethyl 2-cyclopropylacetate

1.87 452.23 B 1.738 2-methyl-N-(oxetan- 3-yl)-N-[[4-[5-(trifiuoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.56 370.16 B 1.739 2,2-difluoro-N- (oxetan-3-yl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.56 404.15 B 1.740 2-chloro-N-(oxetan- 3-yl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.71 438.14 B 1.741 3-methoxy-N-(oxetan- 3-yl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.40 386.18 B 1.742 N-(oxetan-3-yl)- N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

1.62 382.18 B 1.743 1-methyl-N-(oxetan- 3-yl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.56 382.17 B 1.744 3-methyl-N-(oxetan- 3-yl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3-carboxamide

1.38 398.18 B 1.745 2-(methoxymethyl)- N-(oxetan-3-yl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.64 414.23 B 1.746 4-methoxy-N- (oxetan- 3-yl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.50 400.19 B 1.747 N-(oxetan-3-yl)-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamide

1.44 398.19 B 1.748 2-cyano-N-(oxetan- 3-yl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.33 367.14 B 1.749 1-cyano-N-(oxetan- 3-yl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane-carboxamide

1.51 393.15 B 1.750 2-methoxy-N-(oxetan- 3-yl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.42 386.18 B 1.751 3,3,3-trifluoro-N- (oxetan-3-yl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.56 410.15 B 1.752 N-hydroxy-2-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.50 330.13 B 1.753 2,2-difluoroN- hydroxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.51 364.10 B 1.754 2-chloro-N-hydroxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- benzamide

1.60 398.09 B 1.755 [(2-chlorobenzoyl)- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino] 2- chlorobenzoate

2.11 536.12 B 1.756 N-hydroxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-3- carboxamide

1.34 358.13 B 1.757 [tetrahydrofuran-3- carbonyl-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]tetrahydrofuran-3- carboxylate

1.57 456.20 B 1.758 N-hydroxy-3- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.34 346.13 B 1.759 [3-methoxy- propanoyl- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino] 3- methoxypropanoate

1.62 432.19 B 1.760 [propanoyl-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl)phenyl]methyl]- amino] propanoate

1.75 372.17 B 1.761 N-hydroxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclobutane- carboxamide

1.54 342.14 B 1.762 [cyclobutane- carbonyl- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino] cyclobutane- carboxylate

2.03 424.20 B 1.763 N-hydroxy-2-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.53 342.14 B 1.764 N-hydroxy-1-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- cyclopropane- carboxamide

1.50 342.14 B 1.765 N-hydroxy-2-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.60 344.15 B 1.766 N-hyd roxy-3-methyl- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- oxetane-3-c arboxamide

1.34 358.13 B 1.767 [(3-methyloxetane-3- carbonyl)-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino] 3-methyloxelane-3- carboxylate

1.60 456.20 B 1.768 N-hydroxy-2- (methoxymethyl)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.55 374.16 B 1.769 N-hydroxy-4- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.40 360.15 B 1.770 N-hydroxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- tetrahydrofuran-2- carboxamide

1.35 358.13 B 1.771 2-cyano-N-hydroxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.21 327.10 B 1.772 N-hydroxy-2- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.34 346.13 B 1.773 N-hydroxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.27 302.11 B 1.774 2-cyclopropyl-N- hydroxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.50 342.13 B 1.775 [(2-cyclo- propylacetyl)- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino] 2- cyclopropylacetale

1.95 424.21 B 1.776 (acetyl-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino] acetate

1.51 344.12 B 1.777 N-cyclopropyl-2- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.02 356 A 1.778 2-hydroxy-N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

0.93 332 A 1.779 N,2-dimethoxy-2- methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.12 374 A 1.780 2,2,2-trifluoro-N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

1.16 388 A 1.781 2-hydroxy-N,2- dimethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.01 344 A 1.782 2-methoxy-N,2- dimethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.13 359 A 1.783 N-((3-fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl)- N,2-dimethoxy- propanamide

1.04 378 A 1.784 2-hydroxy-N- methoxy-2-methyl- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

1.03 360 A 1.785 2-(difuoromethoxy)- N-methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

0.97 382 A 1.786 2-hydroxy-N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

0.97 346 A 1.787 tert-butyl N-[2- (methoxy-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]-2-oxo- ethyl]carbamate

80- 83.1 1.788 [2-[methoxy-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- amino]-2-oxo- ethyl]ammonium; chloride

0.71 331.5 A 1.789 N-methoxy-N- [[6-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]-3- pyridyl]methyl]- tetrahydrofuran-2-carboxamide

0.9 373 A 1.790 N-[2-[methoxy- [[4-[5-(trifluoro- methyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]- 2-oxo-ethyl]-cyclopropane- carboxamide

135.9- 138.5 1.791 tert-butyl N-[2- (methoxy-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]- 1-methyl-2-oxo-ethyl]carbamate

108.8- 111.9 1.792 [2-[methoxy-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]- 1-methyl-2-oxo-ethyl]ammonium; chloride

200.7- 203.2 1.793 N-[2-[methoxy- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]- 2-oxo- ethyl]propanamide

115.3- 117.8 1.794 2-acetamido-N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

132.8- 134.9 1.795 2-acetamido-N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

0.93 387.3 A 1.796 N-methoxy-2-methyl- N-[[6-[5- (trifluoromethyl)-1,2,4-oxadiazol-3-yl]- 3-pyridyl]methyl]- propanamide

0.98 345 A 1.797 N-methoxy-2- (propanoylamino)-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- propanamide

121.7- 123.9 1.798 N-[2-(methoxy-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]- 1-methyl-2- oxo-ethyl]-cyclopropane- carboxamide

129.7- 134 1.799 tert-butyl 2-[methoxy- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamoyl]- pyrrolldine-1-carboxylate

1.17 471 A 1.800 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pyrrolidin- 1-ium-2- carboxamide;chloride

185.5- 188.5 1.801 2-acetamido-N- methoxy-3-methyl-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

1.02 415 A 1.802 N-methoxy-3-methyl- 2-(propanoylamino)- N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- butanamide

98.5- 100.6 1.803 N-methoxy-1- propanoyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pyrrolidine- 2-carboxamide

148.2- 150.6 1.804 1- (cyclopropane- carbonyl)- N-methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- pyrrolidine-2-carboxamide

1.04 439 A 1.805 1-acetyl-N-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pyrrolidine- 2-carboxamide

93.9- 96.8 1.806 2-bromo-N-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

81.2- 84.9 1.807 ethyl 1-[2-[methoxy- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]- 2-oxo- ethyl]pyrazole-4-carboxylate

79.1- 80.4 1.808 N-methoxy-2-(1,2,4- triazol-1-yl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- acetamide

125.1- 127.2 1.809 N-isopropyl-N-[2-[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- cyclopropane- carboxamide

1.17 368.5 A 1.810 N-cyclopropyl-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- imidazole- 1-carboxamide

0.95 378.5 A 1.811 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- imidazole- 1-carboxamide

0.97 368.4 A

TABLE T2 Melting point (mp) data and/or retention times (RT) forcompounds according to Formula (I): RT MP Entry Name Structure (min)[M + H] Method (° C.) 2.1 ethyl N-methoxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.76 346.2 B 2.2 2-methoxyethyl N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.65 376.2 B 2.3 methyl N-methoxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- caramate

1.07 332 A 2.4 propyl N-methoxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.88 360.2 B 2.5 methyl N-ethoxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

50.6-53 2.6 phenyl N-methoxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.91 394.2 B 2.7 but-2-ynyl N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.80 370.2 B 2.8 isobutyl N-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.98 374.2 B 2.9 pentyl N-methoxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

2.09 388.2 B 2.10 benzyl N-methoxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.96 408.2 B 2.11 allyl N-methoxy-N-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.81 358.2 B 2.12 butyl N-methoxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.98 374.2 B 2.13 4-chlorobutyl N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.92 408.2 B 2.14 isopropyl N-methoxy- N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.86 360.2 B 2.15 2-fluoroethyl N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.66 364.2 B 2.16 3-chloropropyl N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.84 394.2 B 2.17 2-chloroethyl N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.78 380.1 B 2.18 2,2-dimethylpropyl N- methoxy-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

2.07 388.2 B 2.19 (1-chloro-2-methyl- propyl) N-methoxy-N- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

2.06 408.2 B 2.20 prop-2-ynyl N- methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.70 356.2 B 2.21 [tert-butoxycarbonyl- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]tert-butyl carbonate

1.31 476 A 2.22 methyl N-(2,2,2- trifluoroethyl)-N-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.15 400 A 2.23 methyl N-allyl-N- [cyano-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

1.14 367 A 2.24 methyl N-hydroxy-N- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamate

73- 75.1 2.25 [methoxycarbonyl-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- amino]methyl carbonate

1.08 376 A 2.26 methyl N-isopropyl-N- [2-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]ethyl]- carbmate

1.20 358 A

TABLE T3 Melting point (mp) data and/or retention times (RT) forcompounds according to Formula (I): RT MP Entry Name Structure +(min)[M + H] Method (° C.) 3.1 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- morpholine-4- carboxamide

1.54 387.2 B 3.2 1-methoxy-3-(2- methoxyethyl)-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]-urea

1.52 375.17 B 3.3 1,3-dimethoxy-1- methyl-3-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.68 361.16 B 74- 77 3.4 1-methoxy-3-methyl- 1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

75- 78 3.5 1-methoxy-3,3- dimethyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.58 345.2 B 3.6 3- (cyclopropylmethyl)- 1-methoxy-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

77- 81.4 3.7 1-ethoxy-3-methoxy- 3-methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.12 375 A 3.8 1-methoxy-3-phenyl- 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.81 393.2 B 3.9 1-methoxy-3-sec- butyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.78 373.2 B 3.10 3-(2,2- dimethylpropyl)-1- methoxy-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.88 387.2 B 3.11 3-cyclohexyl-1- methoxy-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.92 399.2 B 3.12 3-ethyl-1-methoxy-1- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.56 345.2 B 3.13 3-isobutyl-1-methoxy- 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.78 373.2 B 3.14 3-cyclopropyl-1- methoxy-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.56 357.2 B 84- 87 3.15 3-benzyl-1-methoxy- 1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.77 407.2 B 3.16 3-cyclobutyl-1- methoxy-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.72 371.2 B 3.17 1-ethyl-3-methoxy-1- methyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.70 359.2 B 3.18 3-ethoxy-1-methoxy- 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.50 361.2 B 107- 110 3.19 3-tert-butyl-1- methoxy-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.78 373.2 B 3.20 3-allyl-1-methoxy-1- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.61 357.2 B 3.21 1-methoxy-3-propyl- 1-[[4-[5 - (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.67 359.2 B 3.22 1,3-dimethoxy-1-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.41 347.2 B 88- 91 3.23 3-cyclopentyl-1- methoxy-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.82 385.2 B 3.24 3-(2-furylmethyl)-1- methoxy-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.66 397.2 B 3.25 1-methoxy-1-methyl- 3-(2,2,2-trifluoroethyl)-3-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]urea

1.16 413 A 3.26 1,1-dimethyl-3-(2,2,2- trifluoroethyl)-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.12 397 A 3.27 1-allyl-1-[cyano-[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-3- methoxy-3-methyl- urea

1.12 396 A 3.28 1-ethoxy-3,3- dimethyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.09 359 A 3.29 1-hydroxy-3- methoxy-3-methyl-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

96.3- 100.5 3.30 1-methoxy-1-methyl- 3-propyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.17 373.5 A 3.31 1-[cyano-[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]-3- methoxy-1,3- dimethyl-urea

106- 107 3.32 1-methoxy-1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]urea

112.2- 114.7 3.33 1-cyclopropyl-3- methoxy-3-methyl-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.1 371 A 3.34 1-cyclopropyl-3-ethyl- 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.05 355.4 A 3.35 1-cyclopropyl-3- methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

113- 114 3.36 1,3-dicyclopropyl-1- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.07 367 A 3.37 1,3-dimethyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

95- 98 3.38 1-methoxy-3-(2,2,2- trifluoroethyl)-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

95- 98 3.39 3-(cyanomethyl)-1- methoxy-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

155- 158 3.40 3-[(1- cyanocyclopropyl)- methyl]-1-methoxy-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.03 396 A 3.41 3-[(1S)-1- cyclopropylethyl]-1- methoxy-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

99- 102 3.42 3-isopropyl-1- methoxy-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

106- 107.3 3.43 1-methoxy-3-prop-2- ynyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

88.9- 90.6 3.44 1-[[3-fluoro-4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]-1- methoxy-3-methyl- urea

0.98 349 A 3.45 3-cyclopropyl-1-[[3- fluoro-4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]-1- methoxy-urea

1.03 375 A 3.46 1-methoxy-3-(1- methylcyclopropyl)- 1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

93- 97 3.47 3-(1- cyanocyclopropyl)-1- methoxy-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

106- 109 3.48 ethyl 1-[[methoxy-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamoyl]amino]-cyclopropanecarboxylate

93- 97 3.49 ethyl 2-[[methoxy-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamoyl]- amino]acetate

1.04 403 A 3.50 2-[[methoxy-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamoyl]amino]-N-methyl-acetamide

126- 130 3.51 2-[[methoxy-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]- carbamoyl]amino]- N,N- dimethyl-acetamide

98- 101 3.52 1-ethyl-3-methyl-1- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

0.98 329 A 3.53 3-cyclopropyl-1-ethyl- 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.02 355 A 3.54 3-[(1- hydroxycyclopropyl)- methyl]-1-methoxy-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

107- 110 3.55 1-methoxy-3-(oxetan- 3-yl)-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

97- 100 3.56 3-cyclopropyl-1- methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

113- 121 3.57 1-(cyanomethyl)-3- methoxy-1-methyl-3- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.57 370.2 B 3.58 1-cyclopropyl-3- methoxy-1-methyl-3- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.72 371.2 B 3.59 1-methoxy-3-methyl- 3-(oxetan-3-yl)-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.52 387.2 B 3.60 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pyrrolidine-1- carboxamide

1.72 371.2 B 3.61 1-methoxy-3-methyl- 3-prop-2-ynyl-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.69 369.2 B 3.62 1-cyano-3-methoxy- 1-methyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.61 356.2 B 3.63 1-methoxy-3-(2- methoxyethyl)-3- methyl-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.64 389.2 B 3.64 1,1-diethyl-3- methoxy-3-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.83 373.2 B 3.65 1-cyclobutyl-3- methoxy-1-methyl-3- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.87 385.2 B 3.66 N-methoxy-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- isoxazolidine-2- carboxamide

1.61 373.1 B 3.67 1-(2-methoxyethyl)- 1,3-dimethyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.61 373.2 B 3.68 N-methyl-2-[methyl- [methyl-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamoyl]- amino]acetamide

1.34 386.2 B 3.69 N-methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- isoxazolidine-2- carboxamide

1.63 357.2 B 3.70 1-(cyanomethyl)-1,3- dimethyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.53 354.2 B 3.71 1-cyclopropyl-1-ethyl- 3-methyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.81 369.2 B 3.72 1-cyclopropyl-1,3- dimethyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.70 355.2 B 3.73 ethyl 2-[methyl- [methyl-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamoyl- ]amino]acetate

1.68 401.2 B 3.74 N-methyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pyrrolidine-1- carboxamide

1.70 355.2 B 3.75 1,3-dimethyl-1- propyl-3-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.82 357.2 B 3.76 1-[1- (methoxymethyl)- cyclopropyl]- 1,3-dimethyl-3-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.76 399.2 B 3.77 1,3-dimethyl-1-prop- 2-ynyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.66 353.2 B 3.78 1-allyl-1,3-dimethyl-3- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.77 355.2 B 3.79 1-isopropyl-1,3- dimethyl-3-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.81 357.2 B 3.80 1-cyclopropyl-3- methyl-1-prop-2-ynyl- 3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.75 379.2 B 3.81 1- (cyclopropylmethyl)- 1-ethyl-3-methyl-3- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.95 383.2 B 3.82 1-cyclobutyl-1,3- dimethyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.86 369.2 B 3.83 1- (cyclopropylmethyl)- 1,3-dimethyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.84 369.2 B 3.84 1,1-bis(2- methoxyethyl)-3- methyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.65 417.2 B 3.85 1-ethyl-3-(2- methoxyethyl)-3- methyl-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.73 387.2 B 3.86 2-[[ethyl-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamoyl]-methyl-amino]-N-methyl- acetamide

1.44 400.2 B 3.87 N-ethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- isoxazolidine-2- carboxamide

1.77 371.2 B 3.88 1-(cyanomethyl)-3- ethyl-1-methyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.64 368.2 B 3.89 1-cyclopropyl-1,3- diethyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.91 383.2 B 3.90 1-cyclopropyl-3-ethyl- 1-methyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.81 369.2 B 3.91 1-ethyl-3-methyl-3- (oxetan-3-yl)-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.59 385.2 B 3.92 ethyl 2-[[ethyl-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamoyl]-methyl- amino]acetate

1.79 415.2 B 3.93 N-ethyl-N-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- pyrrolidine-1- carboxamide

1.81 369.2 B 3.94 1-ethyl-3-methyl-3- propyl-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.92 371.2 B 3.95 1-ethyl-3-[1- (methoxymethyl)- cyclopropyl]-3-methyl-1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.86 413.2 B 3.96 1-ethyl-3-methyl-3- prop-2-ynyl-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.77 367.2 B 3.97 1-allyl-3-ethyl-1- methyl-3-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.87 369.2 B 3.98 1-ethyl-3-isopropyl-3- methyl-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.91 371.2 B 3.99 1-cyclopropyl-3-ethyl- 1-prop-2-ynyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.85 393.2 B 3.100 1-(cyclopropylmethyl)- 1,3-diethyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

2.05 397.3 B 3.101 1-cyclobutyl-3-ethyl- 1-methyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.96 383.2 B 3.102 1-ethyl-3,3-bis(2- methoxyethyl)-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.77 431.3 B 3.103 3-[(2,2- difluorocyclopropyl)- methyl]-1-methoxy-1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

81- 84 3.104 1-methoxy-1,3- dimethyl-3-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.69 345.1 B 3.105 1-methyl-3-prop-2- ynyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.48 339.1 B 3.106 1-methyl-3-(2,2,2- trifluoroethyl)-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.65 383.1 B 3.107 3-isopropyl-1-methyl- 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.65 343.1 B 3.108 1-methyl-3-(1- methylcyclopropyl)-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.6 355.2 B 3.109 3-(cyanomethyl)-1- methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.39 340.1 B 3.110 3-(2-methoxyethyl)-1- methyl-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.44 359.2 B 3.111 3-ethyl-1-methyl-1- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.55 329.1 B 3.112 3-cyclobutyl-1- methyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.63 355.2 B 3.113 3-methoxy-1-methyl- 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.37 331.1 B 3.114 3- (cyclopropylmethyl)- 1-methyl-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.63 355.2 B 3.115 1,1-diethyl-3-methyl- 3-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.89 357.2 B 3.116 1-ethyl-3-methoxy-3- methyl-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.79 359.2 B 3.117 1-ethyl-3-prop-2-ynyl- 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.57 353.1 B 3.118 1-ethyl-3-(2,2,2- trifluoroethyl)-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.7 397.2 B 3.119 1-ethyl-3-isopropyl-1- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.7 357.2 B 3.120 1-ethyl-3-(1- methylcyclopropyl)-1- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.7 369.2 B 3.121 3-(cyanomethyl)-1- ethyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.5 354.2 B 3.122 1-ethyl-3-(2- methoxyethyl)-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.55 373.2 B 3.123 1,3-diethyl-1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.6 343.1 B 3.124 3-cyclobutyl-1-ethyl- 1-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.73 369.2 B 3.125 1-ethyl-3-methoxy-1- [[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.48 345.2 B 3.126 1,1,3-triethyl-3-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.98 371.2 B 3.127 1-methoxy-3-methyl- 3-(2,2,2-trifluoroethyl)-1-[[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]urea

1.9 413.2 B 3.128 1-cyclopropyl-1-ethyl- 3-methoxy-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.9 385.2 B 3.129 2-[[methoxy-[[4-[5- (trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamoyl]-methyl-amino]-N-methyl- acetamide

1.4 402.2 B 3.130 ethyl 2-[[methoxy-[[4- [5-(trifluoromethyl)-1,2,4-oxadiazol-3- yl]phenyl]methyl]- carbamoyl]-methyl- amino]acetate

1.75 417.2 B 3.131 1-methoxy-3-methyl- 3-propyl-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.87 373.2 B 3.132 1-isopropyl-3- methoxy-1-methyl-3- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.88 373.2 B 3.133 1-methoxy-3-[1- (methoxymethyl)- cyclopropyl]-3-methyl-1- [[4-[5- (trifluoromethyl)- 1,2,4-oxadiazol-3-yl]phenyl]methyl]urea

1.85 415.2 B 3.134 1-methoxy-3,3-bis(2- methoxyethyl)-1-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.78 433.2 B 3.135 1-allyl-3-methoxy-1- methyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.85 371.2 B 3.136 1-(1-cyanoethyl)-1- cyclopropyl-3- methoxy-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.79 410.2 B 3.137 1- (cyclopropylmethyl)- 1-ethyl-3-methoxy-3- [[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

2 399.2 B 3.138 1-cyclopropyl-3- methoxy-1-prop-2- ynyl-3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.86 395.2 B 3.139 1- (cyclopropylmethyl)- 3-methoxy-1-methyl- 3-[[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]methyl]urea

1.92 385.2 B 3.140 1-isopropyl-3- methoxy-3-methyl-1- [2-[4-[5-(trifluoromethyl)- 1,2,4-oxadiazol-3- yl]phenyl]ethyl]urea

1.18 387.5 A

BIOLOGICAL EXAMPLES

General Examples of Leaf Disk Tests in Well Plates:

Leaf disks or leaf segments of various plant species are cut from plantsgrown in a greenhouse. The cut leaf disks or segments are placed inmultiwell plates (24-well format) onto water agar. The leaf disks aresprayed with a test solution before (preventative) or after (curative)inoculation. Compounds to be tested are prepared as DMSO solutions (max.10 mg/ml) which are diluted to the appropriate concentration with 0.025%Tween20 just before spraying. The inoculated leaf disks or segments areincubated under defined conditions (temperature, relative humidity,light, etc.) according to the respective test system. A singleevaluation of disease level is carried out 3 to 14 days afterinoculation, depending on the pathosystem. Percent disease controlrelative to the untreated check leaf disks or segments is thencalculated.

General Examples of Liquid Culture Tests in Well Plates:

Mycelia fragments or conidia suspensions of a fungus prepared eitherfreshly from liquid cultures of the fungus or from cryogenic storage,are directly mixed into nutrient broth. DMSO solutions of the testcompound (max. 10 mg/ml) are diluted with 0.025% Tween20 by a factor of50 and 10 μl of this solution is pipetted into a microtiter plate(96-well format). The nutrient broth containing the fungalspores/mycelia fragments is then added to give an end concentration ofthe tested compound. The test plates are incubated in the dark at 24° C.and 96% relative humidity. The inhibition of fungal growth is determinedphotometrically after 2 to 7 days, depending on the pathosystem, andpercent antifungal activity relative to the untreated check iscalculated.

Fungicidal Activity Against Puccinia Recondita f. sp. tritici/wheat/leafDisc Preventative (Brown Rust)

Wheat leaf segments cv. Kanzler were placed on agar in multiwell plates(24-well format) and sprayed with the formulated test compound dilutedin water. The leaf disks were inoculated with a spore suspension of thefungus 1 day after application. The inoculated leaf segments wereincubated at 19° C. and 75% relative humidity (rh) under a light regimeof 12 hours light/12 hours darkness in a climate cabinet and theactivity of a compound was assessed as percent disease control comparedto untreated when an appropriate level of disease damage appears inuntreated check leaf segments (7 to 9 days after application).

The following compounds at 200 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol leaf disks under the same conditions, which show extensivedisease development.

Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4, 1.6, 1.8, 1.10, 1.11,1.12, 1.15, 1.16, 1.17, 1.19, 1.20, 1.22, 1.24, 1.25, 1.26, 1.27, 1.28,1.29, 1.30, 1.31, 1.32, 1.33, 1.34, 1.35, 1.36, 1.38, 1.40, 1.41, 1.42,1.43, 1.44, 1.45, 1.46, 1.47, 1.48, 1.49, 1.50, 1.51, 1.52, 1.53, 1.54,1.57, 1.59, 1.60, 1.62, 1.64, 1.67, 1.69, 1.77, 1.81, 1.83, 1.86, 1.87,1.89, 1.90, 1.91, 1.92, 1.93, 1.95, 1.97, 1.99, 1.100, 1.101, 1.102,1.103, 1.104, 1.105, 1.106, 1.107, 1.109, 1.110, 1.111, 1.112, 1.113,1.114, 1.115, 1.117, 1.118, 1.119, 1.120, 1.121, 1.122, 1.123, 1.124,1.125, 1.126, 1.127, 1.128, 1.129, 1.130, 1.132, 1.133, 1.134, 1.135,1.136, 1.138, 1.139, 1.140, 1.141, 1.142, 1.143, 1.144, 1.145, 1.146,1.147, 1.149, 1.150, 1.151, 1.152, 1.154, 1.155, 1.157, 1.158, 1.159,1.161, 1.162, 1.164, 1.165, 1.167, 1.168, 1.169, 1.170, 1.171, 1.172,1.173, 1.175, 1.176, 1.177, 1.178, 1.180, 1.181, 1.182, 1.183, 1.184,1.185, 1.186, 1.187, 1.188, 1.189, 1.190, 1.191, 1.192, 1.193, 1.194,1.196, 1.198, 1.199, 1.200, 1.201, 1.202, 1.205, 1.206, 1.209, 1.212,1.214, 1.215, 1.216, 1.217, 1.218, 1.219, 1.221, 1.222, 1.223, 1.225,1.226, 1.227, 1.229, 1.230, 1.233, 1.234, 1.235, 1.237, 1.238, 1.242,1.243, 1.244, 1.245, 1.247, 1.248, 1.249, 1.250, 1.251, 1.252, 1.253,1.258, 1.259, 1.260, 1.264, 1.266, 1.270, 1.273, 1.274, 1.275, 1.276,1.279, 1.280, 1.283, 1.287, 1.298, 1.305, 1.306, 1.308, 1.309, 1.312,1.313, 1.314, 1.315, 1.316, 1.320, 1.323, 1.324, 1.325, 1.326, 1.327,1.328, 1.329, 1.330, 1.331, 1.332, 1.333, 1.334, 1.335, 1.336, 1.337,1.338, 1.339, 1.340, 1.341, 1.342, 1.344, 1.345, 1.346, 1.347, 1.348,1.350, 1.351, 1.352, 1.353, 1.354, 1.355, 1.356, 1.357, 1.358, 1.359,1.360, 1.361, 1.362, 1.363, 1.364, 1.365, 1.366, 1.367, 1.368, 1.369,1.370, 1.371, 1.372, 1.373, 1.374, 1.375, 1.376, 1.378, 1.379, 1.383,1.384, 1.387, 1.388, 1.389, 1.390, 1.391, 1.392, 1.395, 1.396, 1.398,1.399, 1.400, 1.401, 1.402, 1.403, 1.404, 1.405, 1.406, 1.407, 1.408,1.410, 1.411, 1.412, 1.413, 1.414, 1.415, 1.416, 1.417, 1.418, 1.421,1.422, 1.423, 1.424, 1.426, 1.427, 1.430, 1.431, 1.432, 1.433, 1.434,1.435, 1.436, 1.437, 1.438, 1.440, 1.441, 1.442, 1.443, 1.446, 1.447,1.448, 1.449, 1.450, 1.451, 1.452, 1.453, 1.456, 1.457, 1.458, 1.459,1.460, 1.461, 1.462, 1.463, 1.464, 1.465, 1.466, 1.467, 1.468, 1.469,1.471, 1.472, 1.473, 1.474, 1.475, 1.476, 1.477, 1.478, 1.479, 1.480,1.481, 1.482, 1.483, 1.484, 1.485, 1.486, 1.487, 1.488, 1.489, 1.490,1.491, 1.492, 1.493, 1.494, 1.495, 1.496, 1.497, 1.498, 1.499, 1.500,1.501, 1.502, 1.503, 1.504, 1.505, 1.506, 1.507, 1.508, 1.509, 1.510,1.511, 1.512, 1.513, 1.514, 1.515, 1.516, 1.517, 1.518, 1.519, 1.520,1.521, 1.522, 1.523, 1.524, 1.525, 1.526, 1.527, 1.528, 1.529, 1.530,1.531, 1.532, 1.537, 1.550, 1.552, 1.562, 1.563, 1.564, 1.565, 1.566,1.567, 1.569, 1.570, 1.572, 1.573, 1.574, 1.575, 1.576, 1.577, 1.578,1.579, 1.580, 1.581, 1.582, 1.583, 1.584, 1.585, 1.587, 1.589, 1.590,1.591, 1.592, 1.593, 1.594, 1.595, 1.596, 1.597, 1.598, 1.599, 1.600,1.602, 1.603, 1.604, 1.605, 1.606, 1.607, 1.608, 1.609, 1.610, 1.611,1.612, 1.613, 1.614, 1.615, 1.617, 1.618, 1.619, 1.620, 1.621, 1.622,1.623, 1.624, 1.625, 1.626, 1.627, 1.628, 1.629, 1.631, 1.636, 1.640,1.647, 1.651, 1.652, 1.654, 1.655, 1.656, 1.658, 1.659, 1.660, 1.661,1.662, 1.663, 1.664, 1.665, 1.666, 1.668, 1.669, 1.670, 1.671, 1.672,1.673, 1.674, 1.675, 1.676, 1.677, 1.678, 1.679, 1.680, 1.681, 1.682,1.683, 1.684, 1.685, 1.686, 1.687, 1.688, 1.689, 1.690, 1.692, 1.696,1.698, 1.701, 1.702, 1.703, 1.704, 1.705, 1.707, 1.708, 1.709, 1.711,1.712, 1.713, 1.714, 1.715, 1.716, 1.717, 1.718, 1.720, 1.721, 1.722,1.723, 1.724, 1.725, 1.726, 1.727, 1.728, 1.729, 1.731, 1.732, 1.733,1.734, 1.735, 1.736, 1.737, 1.738, 1.739, 1.740, 1.741, 1.742, 1.743,1.744, 1.745, 1.747, 1.748, 1.749, 1.751, 1.752, 1.753, 1.754, 1.756,1.757, 1.758, 1.759, 1.760, 1.761, 1.762, 1.763, 1.764, 1.765, 1.766,1.767, 1.768, 1.769, 1.770, 1.771, 1.772, 1.773, 1.774, 1.775, 1.776,1.777, 1.778, 1.779, 1.781, 1.782, 1.783, 1.784, 1.785, 1.786, 1.787,1.788, 1.789, 1.790, 1.791, 1.792, 1.793, 1.794, 1.795 and 1.810.

Compounds (from Table T2) 2.1, 2.4, 2.6, 2.7, 2.14, 2.16, 2.21, 2.22,2.24, and 2.25.

Compounds (from Table T3) 3.11, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9,3.10, 3.11, 3.12, 3.13, 3.14, 3.15, 3.16, 3.17, 3.18, 3.19, 3.20, 3.21,3.22, 3.23, 3.24, 3.25, 3.26, 3.28, 3.29, 3.30, 3.31, 3.32, 3.33, 3.34,3.35, 3.36, 3.37, 3.38, 3.39, 3.40, 3.41, 3.42, 3.43, 3.44, 3.45, 3.46,3.47, 3.48, 3.49, 3.50, 3.51, 3.52, 3.53, 3.54, 3.55, 3.56, 3.57, 3.58,3.59, 3.60, 3.61, 3.62, 3.63, 3.64, 3.65, 3.66, 3.67, 3.68, 3.69, 3.70,3.71, 3.72, 3.73, 3.74, 3.75, 3.76, 3.77, 3.78, 3.79, 3.80, 3.81, 3.82,3.83, 3.84, 3.85, 3.86, 3.87, 3.88, 3.89, 3.90, 3.91, 3.92, 3.93, 3.94,3.95, 3.96, 3.97, 3.98, 3.99, 3.101, 3.102, and 3.103.

Fungicidal activity against Puccinia recondita f. sp. tritici/wheat/leafdisc curative (Brown rust

Wheat leaf segments cv. Kanzler are placed on agar in multiwell plates(24-well format). The leaf segments are then inoculated with a sporesuspension of the fungus. Plates were stored in darkness at 19° C. and75% relative humidity. The formulated test compound diluted in water wasapplied 1 day after inoculation. The leaf segments were incubated at 19°C. and 75% relative humidity under a light regime of 12 hours light/12hours darkness in a climate cabinet and the activity of a compound wasassessed as percent disease control compared to untreated when anappropriate level of disease damage appears in untreated check leafsegments (6 to 8 days after application).

The following compounds at 200 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol leaf disks under the same conditions, which show extensivedisease development.

Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4, 1.6, 1.8, 1.10, 1.11,1.12, 1.13, 1.14, 1.15, 1.16, 1.17, 1.19, 1.20, 1.22, 1.23, 1.24, 1.25,1.26, 1.27, 1.28, 1.29, 1.30, 1.31, 1.32, 1.34, 1.35, 1.36, 1.37, 1.38,1.40, 1.41, 1.42, 1.43, 1.44, 1.45, 1.46, 1.47, 1.48, 1.49, 1.50, 1.52,1.53, 1.54, 1.57, 1.59, 1.64, 1.71, 1.77, 1.81, 1.83, 1.86, 1.87, 1.89,1.91, 1.92, 1.95, 1.97, 1.99, 1.100, 1.101, 1.102, 1.103, 1.104, 1.106,1.109, 1.110, 1.111, 1.112, 1.114, 1.115, 1.117, 1.118, 1.119, 1.121,1.122, 1.123, 1.124, 1.125, 1.126, 1.127, 1.128, 1.129, 1.130, 1.131,1.132, 1.134, 1.136, 1.137, 1.138, 1.139, 1.145, 1.146, 1.147, 1.149,1.150, 1.151, 1.153, 1.154, 1.155, 1.157, 1.159, 1.160, 1.161, 1.162,1.164, 1.165, 1.167, 1.168, 1.169, 1.170, 1.171, 1.172, 1.173, 1.175,1.176, 1.177, 1.178, 1.180, 1.181, 1.182, 1.183, 1.185, 1.187, 1.188,1.189, 1.191, 1.192, 1.194, 1.196, 1.199, 1.200, 1.201, 1.202, 1.204,1.206, 1.207, 1.210, 1.215, 1.216, 1.217, 1.223, 1.225, 1.226, 1.227,1.229, 1.230, 1.233, 1.235, 1.237, 1.242, 1.243, 1.244, 1.245, 1.248,1.249, 1.253, 1.259, 1.260, 1.264, 1.266, 1.270, 1.273, 1.275, 1.276,1.279, 1.280, 1.308, 1.309, 1.314, 1.315, 1.316, 1.317, 1.323, 1.324,1.325, 1.326, 1.327, 1.328, 1.329, 1.330, 1.331, 1.332, 1.333, 1.334,1.335, 1.336, 1.337, 1.339, 1.340, 1.341, 1.344, 1.345, 1.346, 1.347,1.348, 1.349, 1.350, 1.351, 1.353, 1.355, 1.356, 1.357, 1.358, 1.359,1.360, 1.361, 1.362, 1.363, 1.364, 1.365, 1.366, 1.368, 1.369, 1.370,1.371, 1.372, 1.373, 1.374, 1.375, 1.377, 1.378, 1.379, 1.383, 1.384,1.387, 1.388, 1.389, 1.390, 1.391, 1.392, 1.395, 1.396, 1.398, 1.399,1.400, 1.401, 1.402, 1.403, 1.404, 1.406, 1.407, 1.408, 1.411, 1.412,1.415, 1.417, 1.421, 1.422, 1.426, 1.427, 1.431, 1.432, 1.433, 1.434,1.435, 1.438, 1.442, 1.443, 1.444, 1.445, 1.446, 1.447, 1.448, 1.450,1.451, 1.452, 1.455, 1.456, 1.457, 1.458, 1.459, 1.460, 1.463, 1.465,1.466, 1.467, 1.468, 1.469, 1.472, 1.473, 1.474, 1.476, 1.477, 1.478,1.479, 1.480, 1.481, 1.483, 1.484, 1.485, 1.486, 1.487, 1.488, 1.489,1.490, 1.491, 1.492, 1.493, 1.494, 1.495, 1.496, 1.497, 1.498, 1.499,1.500, 1.501, 1.502, 1.503, 1.504, 1.505, 1.506, 1.507, 1.508, 1.509,1.510, 1.511, 1.512, 1.513, 1.514, 1.515, 1.516, 1.517, 1.518, 1.519,1.520, 1.521, 1.522, 1.523, 1.524, 1.525, 1.526, 1.527, 1.528, 1.529,1.530, 1.531, 1.532, 1.563, 1.564, 1.566, 1.567, 1.568, 1.569, 1.570,1.571, 1.573, 1.574, 1.575, 1.577, 1.578, 1.579, 1.580, 1.582, 1.583,1.584, 1.585, 1.586, 1.587, 1.589, 1.590, 1.591, 1.592, 1.593, 1.594,1.595, 1.596, 1.597, 1.599, 1.600, 1.603, 1.604, 1.605, 1.606, 1.607,1.608, 1.609, 1.610, 1.611, 1.612, 1.613, 1.614, 1.615, 1.617, 1.618,1.620, 1.621, 1.622, 1.623, 1.624, 1.625, 1.626, 1.629, 1.631, 1.640,1.651, 1.652, 1.654, 1.655, 1.656, 1.658, 1.659, 1.660, 1.661, 1.662,1.663, 1.664, 1.665, 1.666, 1.667, 1.668, 1.669, 1.670, 1.671, 1.673,1.674, 1.675, 1.676, 1.677, 1.678, 1.679, 1.680, 1.681, 1.682, 1.683,1.684, 1.685, 1.686, 1.687, 1.688, 1.689, 1.690, 1.692, 1.693, 1.696,1.698, 1.701, 1.702, 1.703, 1.705, 1.707, 1.711, 1.712, 1.713, 1.714,1.717, 1.718, 1.721, 1.722, 1.723, 1.724, 1.725, 1.726, 1.727, 1.731,1.732, 1.738, 1.739, 1.740, 1.741, 1.742, 1.743, 1.744, 1.745, 1.747,1.748, 1.749, 1.750, 1.751, 1.752, 1.753, 1.756, 1.757, 1.758, 1.759,1.760, 1.761, 1.762, 1.763, 1.764, 1.765, 1.766, 1.767, 1.768, 1.769,1.770, 1.771, 1.772, 1.773, 1.774, 1.775, 1.776, 1.777, 1.778, 1.779,1.781, 1.782, 1.783, 1.784, 1.785, 1.786, 1.787, 1.788, 1.789, 1.790,1.791, 1.792, 1.793, 1.794, 1.795 and 1.810.

Compounds (from Table T2) 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.11, 2.14,2.15, 2.16, 2.17, 2.20, 2.22, 2.24, and 2.25.

Compounds (from Table T3) 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9,3.10, 3.12, 3.13, 3.14, 3.15, 3.16, 3.17, 3.18, 3.19, 3.20, 3.21, 3.22,3.23, 3.24, 3.25, 3.26, 3.28, 3.29, 3.30, 3.31, 3.32, 3.33, 3.34, 3.36,3.37, 3.38, 3.39, 3.40, 3.41, 3.42, 3.43, 3.44, 3.45, 3.46, 3.47, 3.48,3.49, 3.50, 3.51, 3.52, 3.53, 3.54, 3.55, 3.56, 3.57, 3.58, 3.59, 3.60,3.61, 3.63, 3.64, 3.65, 3.67, 3.68, 3.69, 3.70, 3.71, 3.72, 3.73, 3.74,3.75, 3.76, 3.77, 3.78, 3.79, 3.80, 3.81, 3.82, 3.83, 3.84, 3.85, 3.86,3.87, 3.88, 3.89, 3.90, 3.91, 3.92, 3.93, 3.94, 3.95, 3.97, 3.98, 3.99,3.100, 3.101, 3.102, and 3.103.

Fungicidal Activity Against Phakopsora pachyrhizi/Soybean/Leaf DiscPreventative (Asian Soybean Rust)

Soybean leaf disks are placed on water agar in multiwell plates (24-wellformat) and sprayed with the formulated test compound diluted in water.One day after application leaf discs are inoculated by spraying a sporesuspension on the lower leaf surface. After an incubation period in aclimate cabinet of 24-36 hours in darkness at 20° C. and 75% rh leafdisc are kept at 20° C. with 12 h light/day and 75% rh. The activity ofa compound is assessed as percent disease control compared to untreatedwhen an appropriate level of disease damage appears in untreated checkleaf disks (12 to 14 days after application).

The following compounds at 200 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol leaf disks under the same conditions, which show extensivedisease development.

Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.8, 1.11, 1.12,1.14, 1.15, 1.16, 1.17, 1.19, 1.20, 1.22, 1.23, 1.24, 1.26, 1.27, 1.28,1.29, 1.30, 1.31, 1.32, 1.33, 1.34, 1.35, 1.36, 1.38, 1.40, 1.41, 1.42,1.43, 1.44, 1.45, 1.46, 1.47, 1.48, 1.49, 1.50, 1.51, 1.53, 1.54, 1.57,1.58, 1.59, 1.60, 1.64, 1.71, 1.77, 1.81, 1.82, 1.83, 1.84, 1.86, 1.87,1.89, 1.90, 1.91, 1.92, 1.93, 1.95, 1.97, 1.99, 1.100, 1.101, 1.102,1.103, 1.104, 1.106, 1.109, 1.110, 1.111, 1.112, 1.114, 1.115, 1.117,1.118, 1.119, 1.121, 1.122, 1.123, 1.124, 1.125, 1.126, 1.128, 1.130,1.132, 1.134, 1.135, 1.136, 1.138, 1.144, 1.145, 1.146, 1.147, 1.149,1.150, 1.151, 1.154, 1.155, 1.157, 1.158, 1.159, 1.164, 1.165, 1.166,1.167, 1.168, 1.169, 1.170, 1.171, 1.172, 1.173, 1.175, 1.176, 1.177,1.178, 1.180, 1.181, 1.182, 1.183, 1.185, 1.187, 1.189, 1.190, 1.191,1.192, 1.193, 1.194, 1.195, 1.196, 1.197, 1.199, 1.200, 1.201, 1.202,1.206, 1.207, 1.209, 1.210, 1.212, 1.215, 1.216, 1.217, 1.218, 1.220,1.221, 1.222, 1.223, 1.224, 1.226, 1.227, 1.229, 1.230, 1.233, 1.235,1.238, 1.241, 1.242, 1.243, 1.244, 1.245, 1.246, 1.253, 1.264, 1.273,1.274, 1.275, 1.309, 1.312, 1.314, 1.315, 1.316, 1.324, 1.325, 1.327,1.329, 1.331, 1.335, 1.337, 1.339, 1.341, 1.342, 1.344, 1.345, 1.346,1.350, 1.351, 1.355, 1.356, 1.358, 1.359, 1.360, 1.361, 1.363, 1.365,1.368, 1.369, 1.372, 1.379, 1.383, 1.384, 1.387, 1.389, 1.390, 1.392,1.395, 1.398, 1.399, 1.401, 1.402, 1.403, 1.404, 1.407, 1.408, 1.412,1.416, 1.418, 1.432, 1.457, 1.466, 1.471, 1.472, 1.475, 1.476, 1.477,1.478, 1.479, 1.480, 1.483, 1.484, 1.485, 1.486, 1.487, 1.488, 1.489,1.491, 1.492, 1.493, 1.494, 1.495, 1.496, 1.497, 1.498, 1.499, 1.500,1.503, 1.504, 1.505, 1.506, 1.507, 1.508, 1.509, 1.510, 1.511, 1.512,1.513, 1.514, 1.515, 1.516, 1.517, 1.518, 1.519, 1.520, 1.521, 1.523,1.524, 1.525, 1.526, 1.527, 1.528, 1.529, 1.531, 1.532, 1.562, 1.563,1.564, 1.566, 1.567, 1.568, 1.569, 1.570, 1.571, 1.573, 1.574, 1.575,1.576, 1.577, 1.578, 1.579, 1.580, 1.581, 1.582, 1.583, 1.584, 1.585,1.586, 1.587, 1.589, 1.590, 1.591, 1.592, 1.594, 1.595, 1.596, 1.597,1.599, 1.600, 1.603, 1.604, 1.605, 1.606, 1.607, 1.608, 1.610, 1.611,1.612, 1.613, 1.614, 1.615, 1.616, 1.617, 1.618, 1.619, 1.620, 1.621,1.622, 1.623, 1.624, 1.625, 1.626, 1.627, 1.628, 1.629, 1.630, 1.631,1.632, 1.634, 1.636, 1.637, 1.639, 1.640, 1.641, 1.642, 1.643, 1.644,1.645, 1.646, 1.647, 1.648, 1.649, 1.651, 1.652, 1.653, 1.654, 1.655,1.656, 1.657, 1.658, 1.659, 1.660, 1.661, 1.662, 1.663, 1.664, 1.665,1.666, 1.667, 1.668, 1.669, 1.670, 1.671, 1.672, 1.673, 1.674, 1.675,1.676, 1.677, 1.678, 1.679, 1.680, 1.681, 1.682, 1.683, 1.684, 1.685,1.686, 1.687, 1.688, 1.689, 1.690, 1.691, 1.692, 1.693, 1.694, 1.695,1.696, 1.697, 1.698, 1.699, 1.700, 1.701, 1.702, 1.703, 1.704, 1.705,1.706, 1.707, 1.708, 1.709, 1.710, 1.711, 1.712, 1.714, 1.715, 1.716,1.717, 1.718, 1.720, 1.721, 1.722, 1.723, 1.724, 1.725, 1.726, 1.727,1.728, 1.729, 1.730, 1.731, 1.732, 1.733, 1.734, 1.735, 1.736, 1.737,1.738, 1.739, 1.740, 1.741, 1.742, 1.743, 1.744, 1.745, 1.746, 1.747,1.748, 1.749, 1.750, 1.751, 1.752, 1.753, 1.754, 1.755, 1.756, 1.757,1.758, 1.759, 1.760, 1.761, 1.762, 1.763, 1.764, 1.765, 1.766, 1.767,1.768, 1.769, 1.770, 1.771, 1.772, 1.773, 1.774, 1.775, 1.776, 1.777,1.778, 1.779, 1.781, 1.782, 1.783, 1.784, 1.786 and 1.810.

Compounds (from Table T2) 2.2, 2.3, 2.4, 2.5, 2.21, 2.24, and 2.25.

Compounds (from Table T3) 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9,3.11, 3.12, 3.13, 3.14, 3.15, 3.16, 3.17, 3.18, 3.19, 3.20, 3.21, 3.22,3.23, 3.24, 3.25, 3.26, 3.28, 3.29, 3.30, 3.31, 3.32, 3.33, 3.34, 3.36,3.37, 3.38, 3.39, 3.40, 3.41, 3.42, 3.43, 3.44, 3.45, 3.46, 3.47, 3.48,3.51, 3.52, 3.53, 3.55, 3.56, 3.57, 3.58, 3.59, 3.60, 3.61, and 3.62.

Fungicidal Activity Against Glomerella lagenarium (Colletotrichumlagenarium) Liquid Culture/Cucumber/Preventative (Anthracnose)

Conidia of the fungus from cryogenic storage are directly mixed intonutrient broth (PDB-potato dextrose broth). After placing a (DMSO)solution of test compound into a microtiter plate (96-well format), thenutrient broth containing the fungal spores is added. The test platesare incubated at 24° C. and the inhibition of growth is measuredphotometrically 3 to 4 days after application.

The following compounds at 20 ppm in the applied formulation give atleast 80% disease control in this test when compared to untreatedcontrol under the same conditions, which show extensive diseasedevelopment.

Compounds (from Table T1) 1.1, 1.2, 1.3, 1.4, 1.5, 1.6, 1.7, 1.8, 1.9,1.10, 1.11, 1.12, 1.13, 1.15, 1.16, 1.17, 1.18, 1.19, 1.20, 1.22, 1.23,1.24, 1.25, 1.26, 1.27, 1.28, 1.29, 1.30, 1.31, 1.32, 1.33, 1.34, 1.35,1.36, 1.37, 1.38, 1.40, 1.41, 1.42, 1.43, 1.44, 1.45, 1.46, 1.47, 1.48,1.49, 1.50, 1.51, 1.53, 1.54, 1.55, 1.57, 1.58, 1.59, 1.61, 1.64, 1.67,1.68, 1.69, 1.71, 1.72, 1.74, 1.77, 1.81, 1.82, 1.83, 1.84, 1.85, 1.86,1.87, 1.88, 1.89, 1.90, 1.91, 1.92, 1.93, 1.94, 1.95, 1.96, 1.97, 1.98,1.99, 1.100, 1.101, 1.102, 1.103, 1.104, 1.105, 1.106, 1.107, 1.108,1.109, 1.110, 1.111, 1.112, 1.113, 1.114, 1.115, 1.116, 1.117, 1.118,1.119, 1.120, 1.121, 1.122, 1.123, 1.124, 1.125, 1.126, 1.127, 1.128,1.129, 1.130, 1.131, 1.132, 1.133, 1.134, 1.135, 1.136, 1.138, 1.139,1.142, 1.144, 1.145, 1.146, 1.147, 1.148, 1.149, 1.150, 1.151, 1.152,1.153, 1.154, 1.155, 1.157, 1.158, 1.159, 1.161, 1.162, 1.163, 1.164,1.165, 1.166, 1.167, 1.168, 1.169, 1.170, 1.171, 1.173, 1.174, 1.175,1.176, 1.177, 1.178, 1.179, 1.180, 1.181, 1.182, 1.183, 1.184, 1.185,1.187, 1.189, 1.190, 1.191, 1.192, 1.193, 1.194, 1.195, 1.196, 1.199,1.201, 1.202, 1.203, 1.205, 1.206, 1.207, 1.208, 1.209, 1.210, 1.211,1.212, 1.213, 1.214, 1.215, 1.216, 1.217, 1.218, 1.219, 1.220, 1.221,1.222, 1.223, 1.224, 1.225, 1.226, 1.227, 1.228, 1.229, 1.230, 1.231,1.232, 1.233, 1.235, 1.236, 1.237, 1.238, 1.239, 1.240, 1.242, 1.243,1.244, 1.245, 1.246, 1.247, 1.248, 1.249, 1.250, 1.251, 1.252, 1.253,1.254, 1.255, 1.256, 1.257, 1.258, 1.259, 1.260, 1.261, 1.262, 1.264,1.265, 1.266, 1.268, 1.269, 1.270, 1.271, 1.272, 1.273, 1.274, 1.275,1.276, 1.277, 1.278, 1.279, 1.280, 1.281, 1.282, 1.283, 1.284, 1.285,1.286, 1.287, 1.288, 1.289, 1.290, 1.291, 1.292, 1.293, 1.294, 1.295,1.297, 1.298, 1.299, 1.301, 1.302, 1.303, 1.304, 1.305, 1.306, 1.307,1.308, 1.309, 1.310, 1.311, 1.312, 1.313, 1.314, 1.315, 1.316, 1.317,1.318, 1.319, 1.320, 1.321, 1.322, 1.323, 1.324, 1.325, 1.326, 1.327,1.328, 1.329, 1.330, 1.331, 1.332, 1.333, 1.334, 1.335, 1.336, 1.337,1.338, 1.339, 1.340, 1.341, 1.342, 1.343, 1.344, 1.345, 1.346, 1.347,1.348, 1.349, 1.350, 1.351, 1.352, 1.355, 1.356, 1.358, 1.359, 1.360,1.361, 1.362, 1.363, 1.364, 1.365, 1.366, 1.367, 1.368, 1.369, 1.370,1.371, 1.372, 1.373, 1.374, 1.375, 1.376, 1.377, 1.378, 1.379, 1.380,1.381, 1.382, 1.384, 1.385, 1.387, 1.388, 1.389, 1.390, 1.391, 1.392,1.393, 1.394, 1.395, 1.396, 1.397, 1.398, 1.399, 1.400, 1.401, 1.402,1.403, 1.404, 1.405, 1.406, 1.407, 1.408, 1.409, 1.410, 1.411, 1.412,1.413, 1.414, 1.415, 1.416, 1.417, 1.418, 1.419, 1.420, 1.421, 1.422,1.423, 1.424, 1.425, 1.426, 1.427, 1.428, 1.429, 1.430, 1.431, 1.432,1.433, 1.434, 1.435, 1.436, 1.437, 1.438, 1.439, 1.440, 1.442, 1.443,1.445, 1.446, 1.447, 1.448, 1.449, 1.450, 1.451, 1.452, 1.453, 1.455,1.456, 1.457, 1.458, 1.459, 1.460, 1.461, 1.462, 1.463, 1.464, 1.465,1.466, 1.467, 1.468, 1.469, 1.470, 1.471, 1.472, 1.473, 1.474, 1.475,1.476, 1.477, 1.478, 1.479, 1.480, 1.481, 1.482, 1.483, 1.484, 1.485,1.486, 1.487, 1.488, 1.489, 1.490, 1.491, 1.492, 1.493, 1.494, 1.495,1.496, 1.497, 1.498, 1.499, 1.500, 1.501, 1.502, 1.503, 1.504, 1.505,1.506, 1.507, 1.508, 1.509, 1.510, 1.511, 1.512, 1.513, 1.514, 1.515,1.516, 1.517, 1.518, 1.519, 1.520, 1.521, 1.522, 1.523, 1.524, 1.525,1.526, 1.527, 1.528, 1.529, 1.530, 1.531, 1.532, 1.533, 1.534, 1.535,1.536, 1.537, 1.538, 1.539, 1.540, 1.541, 1.542, 1.543, 1.544, 1.545,1.546, 1.547, 1.548, 1.549, 1.550, 1.551, 1.553, 1.554, 1.555, 1.556,1.557, 1.558, 1.559, 1.560, 1.561, 1.562, 1.563, 1.564, 1.565, 1.566,1.567, 1.568, 1.569, 1.570, 1.571, 1.572, 1.573, 1.574, 1.575, 1.576,1.577, 1.578, 1.579, 1.580, 1.581, 1.582, 1.583, 1.584, 1.585, 1.586,1.587, 1.588, 1.589, 1.590, 1.591, 1.592, 1.593, 1.594, 1.595, 1.596,1.597, 1.598, 1.599, 1.600, 1.601, 1.602, 1.603, 1.604, 1.605, 1.606,1.607, 1.608, 1.609, 1.610, 1.611, 1.612, 1.613, 1.614, 1.615, 1.616,1.617, 1.618, 1.619, 1.620, 1.621, 1.622, 1.623, 1.624, 1.625, 1.626,1.627, 1.628, 1.629, 1.630, 1.631, 1.632, 1.633, 1.634, 1.636, 1.637,1.638, 1.639, 1.641, 1.642, 1.643, 1.644, 1.645, 1.646, 1.647, 1.648,1.649, 1.650, 1.651, 1.652, 1.653, 1.654, 1.655, 1.656, 1.657, 1.658,1.659, 1.660, 1.661, 1.662, 1.663, 1.664, 1.665, 1.666, 1.667, 1.668,1.669, 1.670, 1.671, 1.672, 1.673, 1.674, 1.675, 1.676, 1.677, 1.678,1.679, 1.680, 1.681, 1.682, 1.683, 1.684, 1.685, 1.686, 1.687, 1.688,1.689, 1.690, 1.691, 1.692, 1.693, 1.694, 1.695, 1.696, 1.697, 1.698,1.699, 1.700, 1.701, 1.702, 1.703, 1.704, 1.705, 1.706, 1.707, 1.708,1.709, 1.713, 1.714, 1.715, 1.716, 1.717, 1.718, 1.720, 1.723, 1.724,1.725, 1.726, 1.727, 1.729, 1.730, 1.733, 1.734, 1.735, 1.736, 1.737,1.738, 1.739, 1.740, 1.741, 1.742, 1.743, 1.745, 1.749, 1.751, 1.752,1.753, 1.754, 1.755, 1.756, 1.757, 1.758, 1.759, 1.760, 1.761, 1.762,1.763, 1.764, 1.765, 1.766, 1.768, 1.769, 1.770, 1.771, 1.772, 1.773,1.774, 1.775, 1.776, 1.777, 1.778, 1.779, 1.780, 1.781, 1.782, 1.783,1.784, 1.785, 1.786, 1.787, 1.790, 1.791, 1.793, 1.794, 1.795, 1.810 and1.811.

Compounds (from Table T2) 2.1, 2.2, 2.3, 2.4, 2.5, 2.6, 2.7, 2.8, 2.9,2.10, 2.11, 2.12, 2.13, 2.14, 2.15, 2.16, 2.17, 2.18, 2.19, 2.20, 2.21,2.22, 2.24, and 2.25.

Compounds (from Table T3) 3.1, 3.2, 3.3, 3.4, 3.5, 3.6, 3.7, 3.8, 3.9,3.10, 3.11, 3.12, 3.13, 3.14, 3.15, 3.16, 3.17, 3.18, 3.19, 3.20, 3.21,3.22, 3.23, 3.24, 3.25, 3.26, 3.28, 3.29, 3.30, 3.31, 3.32, 3.33, 3.34,3.35, 3.36, 3.37, 3.38, 3.39, 3.40, 3.41, 3.42, 3.43, 3.44, 3.45, 3.46,3.47, 3.48, 3.49, 3.51, 3.52, 3.53, 3.54, 3.55, 3.56, 3.57, 3.58, 3.59,3.60, 3.61, 3.62, 3.63, 3.64, 3.65, 3.66, 3.67, 3.69, 3.70, 3.71, 3.72,3.73, 3.74, 3.75, 3.76, 3.77, 3.78, 3.79, 3.80, 3.81, 3.82, 3.83, 3.84,3.85, 3.87, 3.88, 3.89, 3.90, 3.91, 3.92, 3.93, 3.94, 3.95, 3.96, 3.97,3.98, 3.99, 3.100, 3.101, 3.102, and 3.103.

The invention claimed is:
 1. A compound of formula (I):

wherein R¹ and R² are independently selected from hydrogen, chloro,fluoro, methyl, methoxy and trifluoromethyl; and R³ and R⁴ areindependently selected from hydrogen and halogen; wherein at least twoof R¹, R², R³ and R⁴ are hydrogen; R⁵ and R⁶ are independently selectedfrom hydrogen and C₁₋₄alkyl; R⁷ is C₁₋₄alkyl or C₁₋₄alkoxy; and R⁸ ishydrogen, C₁₋₆alkyl, C₂₋₆alkenyl, C₂₋₆alkynyl, cyanoC₁₋₆alkyl,C₁₋₆haloalkyl, C₁₋₆haloalkenyl, hydroxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₆alkyl,C₁₋₄haloalkoxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl,C₂₋₄alkynyloxyC₁₋₆alkyl, aminoC₁₋₆alkyl, N—C₁₋₄alkylaminoC₁₋₆alkyl,N,N-diC₁₋₄alkylaminoC₁₋₆alkyl, C₁₋₆alkylcarbonylC₁₋₆alkyl,C₁₋₆alkylcarbonylC₂₋₆alkenyl, C₁₋₆alkoxycarbonylC₁₋₆alkyl,C₁₋₆alkylcarbonyloxyC₁₋₆alkyl, N—C₁₋₄alkylaminocarbonylC₁₋₆alkyl,N,N-diC₁₋₄alkylaminocarbonylC₁₋₆alkyl, C₁₋₆alkylsulfanylC₁₋₆alkyl,C₁₋₆alkylsulfonylC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₂₋₆alkynyl, or C₂₋₆alkynyloxycarbonylaminoC₁₋₆alkyl;or R⁸ is C₃₋₈cycloalkylC₀₋₆alkyl, wherein the cycloalkyl moiety isoptionally partially unsaturated, phenylC₀₋₆alkyl, phenylC₂₋₆alkenyl,naphthylC₀₋₆alkyl, heteroarylC₀₋₆alkyl wherein the heteroaryl moiety isa 5- or 6-membered monocyclic aromatic ring which comprises 1, 2, 3 or 4heteroatoms individually selected from N, O and S, heterodiarylC₀₋₆alkylwherein the heterodiaryl moiety is a 9- or 10-membered bicyclic aromaticsystem which comprises 1, 2, 3 or 4 heteroatoms individually selectedfrom N, O and S, heterocyclylC₀₋₆alkyl wherein the heterocyclyl moietyis a 4-to 6-membered non-aromatic ring which comprises 1, 2 or 3heteroatoms individually selected from N, O and S, orC₃₋₆cycloalkylcarbonylaminoC₁₋₆alkyl, wherein for R⁸, any ofC₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl, phenylC₂₋₆alkenyl,naphthylC₀₋₆alkyl, heteroarylC₀₋₆alkyl, heterodiarylC₀₋₆alkyl,heterocyclylC₀₋₆alkyl and C₃₋₆cycloalkylcarbonylaminoC₁₋₆alkyl moietiesare optionally substituted by 1, 2 or 3 substituents, which may be thesame or different, selected from R⁹; wherein R⁹ represents cyano,halogen, hydroxy, C₁₋₄alkyl, C₂₋₄alkenyl, C₂₋₄alkynyl, C₁₋₄haloalkyl,C₂₋₄haloalkenyl, C₁₋₄alkoxy, C₁₋₄haloalkoxy, C₃₋₄alkynyloxy,N—C₁₋₄alkylamino, N,N-diC₁₋₄alkylamino, C₁₋₄alkylcarbonyl,C₁₋₄alkoxycarbonyl, carbonylamino, N—C₁₋₄alkylaminocarbonyl,N,N-diC₁₋₄alkylaminocarbonyl or C₁₋₄alkoxycarbonylamino, and whereinwhen R₈ is substituted C₃₋₈cycloalkylC₀₋₆alkyl or heterocyclylC₀₋₆alkyl,R⁹ may also represent oxo on the C₃₋₈cycloalkyl or heterocyclyl moiety;or wherein for R⁸, any of C₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl,phenylC₂₋₆alkenyl, naphthylC₀₋₆alkyl, heteroarylC₀₋₆alkyl,heterodiarylC₀₋₆alkyl, heterocyclylC₀₋₆alkyl andC₃₋₆cycloalkylcarbonylaminoC₁₋₆alkyl moieties are optionally substitutedby 1 substituent selected from R¹⁰; wherein R¹⁰ representsC₃₋₈cycloalkylC₀₋₂alkyl, phenylC₀₋₂alkyl, heteroarylC₀₋₂alkyl whereinthe heteroaryl moiety is a 5- or 6-membered monocyclic aromatic ringwhich comprises 1, 2, 3 or 4 heteroatoms individually selected from N, Oand S, heterocyclylC₀₋₆alkyl wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S, and wherein any of saidcycloalkyl, phenyl, heteroaryl and heterocyclyl moieties are optionallysubstituted by 1, 2 or 3 substituents, which may be the same ordifferent, selected from R¹¹; wherein R¹¹ represents hydrogen, cyano,fluoro, chloro, bromo, methyl, trifluoromethyl, methoxy and ethoxy; or asalt or an N-oxide thereof.
 2. The compound according to claim 1,wherein R⁸ represents hydrogen, C₁₋₆alkyl, C₂₋₆alkenyl, C₂₋₆alkynyl,cyanoC₁₋₆alkyl, C₁₋₆haloalkyl, C₁₋₆haloalkenyl, hydroxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₄haloalkoxyC₁₋₆alkyl,C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl, C₂₋₄alkynyloxyC₁₋₆alkyl,C₁₋₆alkylcarbonylC₂₋₆alkenyl, C₁₋₆alkylcarbonyloxyC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₂₋₆alkynyl, C₂₋₆alkynyloxycarbonylaminoC₁₋₆alkyl; orC₃₋₈cycloalkylC₀₋₂alkyl, wherein the cycloalkyl moiety is optionallypartially unsaturated, phenylC₀₋₂alkyl, heteroarylC₀₋₂alkyl wherein theheteroaryl moiety is a 5- or 6-membered monocyclic aromatic ring whichcomprises 1, 2, 3 or 4 heteroatoms individually selected from N, O andS, or heterocyclylC₀₋₂alkyl wherein the heterocyclyl moiety is a 4- to6-membered non-aromatic ring which comprises 1, 2 or 3 heteroatomsindividually selected from N, O and S; wherein any of saidC₃₋₈cycloalkylC₀₋₂alkyl, phenylC₀₋₂alkyl, heteroarylC₀₋₂alkyl andheterocyclylC₀₋₂alkyl moieties are optionally substituted by 1, 2 or 3substituents, which may be the same or different, selected from R⁹; andR⁹ represents cyano, halogen, hydroxy, C₁₋₄alkyl, C₁₋₄haloalkyl,C₁₋₄alkoxy, C₂₋₄haloalkenyl, C₃₋₄alkynyloxy, C₁₋₄alkylcarbonyl andC₁₋₄alkoxycarbonyl.
 3. The compound according to claim 1, wherein R⁸represents C₁₋₆alkyl, C₂₋₆alkenyl, C₂₋₆alkynyl, C₁₋₆fluoroalkyl,C₁₋₆chloroalkyl, C₁₋₄alkoxyC₁₋₆alkyl, C₁₋₄alkoxyC₁₋₄alkoxyC₁₋₆alkyl,C₁₋₆alkylcarbonylC₂₋₆alkenyl, C₁₋₆alkylcarbonyloxyC₁₋₆alkyl, C₁₋₆alkylsulfonylaminoC₂₋₆alkynyl or C₂₋₆alkynyloxycarbonylaminoC₁₋₆alkyl.4. The compound according to claim 1, wherein R⁸ representsC₃₋₈cycloalkylC₀₋₆alkyl, phenylC₀₋₆alkyl, or heterocyclylC₀₋₆alkyl,wherein any of said cycloalkyl, phenyl, and heterocyclyl moieties areoptionally substituted by 1, 2 or 3 substituents which may be the sameor different, selected from R⁹, wherein R⁹ is cyano, halogen, hydroxy,C₁₋₄alkyl, C₁₋₄haloalkyl, C₂₋₄haloalkenyl, C₃₋₄alkynyloxy,C₁₋₄alkylcarbonyl, C₁₋₄alkoxycarbonyl; or wherein any of saidcycloalkyl, phenyl, and heterocyclyl moieties are optionally substitutedby 1 substituent selected from R¹⁰ which is a phenyl.
 5. The compoundaccording to claim 4, wherein R⁸ represents C₃₋₆cycloalkylC₀₋₁alkyl,phenylC₀₋₁alkyl or heterocyclylC₀₋₁alkyl, wherein any of saidcycloalkyl, phenyl, and heterocyclyl moieties are optionally substitutedby 1, 2 or 3 substituents which may be the same or different, selectedfrom R⁹, wherein R⁹ is cyano, fluoro, chloro, hydroxy, methyl, ethyl,trifluoromethyl, 2,2-dichloroethenyl, propynyloxy, acetyl,methoxycarbonyl; or wherein any of said cycloalkyl, phenyl, andheterocyclyl moieties are optionally substituted by 1 substituentselected from R¹⁰ which is a phenyl.
 6. The compound according to claim1, wherein R¹ and R² are independently selected from hydrogen andfluorine.
 7. The compound according to claim 1, wherein R³ and R⁴ areindependently selected from hydrogen and fluorine.
 8. The compoundaccording to claim 1, wherein R⁵ and R⁶ are hydrogen, or R⁵ is hydrogenand R⁶ is methyl.
 9. The compound according to claim 1, wherein R⁷represents methoxy, propoxy or sec-butyl.
 10. The compound according toclaim 1, said compound being selected from:


11. An agrochemical composition comprising a fungicidally effectiveamount of a compound of formula (I) according to claim
 1. 12. Acomposition according to claim 11, further comprising at least oneadditional active ingredient and/or an agrochemically-acceptable diluentor carrier.
 13. A method of controlling or preventing infestation ofuseful plants by phytopathogenic microorganisms, wherein a fungicidallyeffective amount of a compound of formula (I) according to claim 1, or acomposition comprising this compound as active ingredient, is applied tothe plants, to parts thereof or the locus thereof.